Tottenham Hotspur

Tottenham Hotspur versus Everton is a special fixture for Darren Caskey.

Back on 3 October, 1993, the Toffees provided the opposition as the Basildon-born midfielder, who had previously made seven substitute appearances for us, started in a senior competitive match for the first time. This memorable occasion was capped by Caskey scoring a stoppage-time winner at the end of the 90 minutes as we triumphed 3-2 in a Premier League match.

That 1993/94 season was a fine breakthrough one for Caskey, who scored five goals in 32 appearances in all competitions, aged just 19 at the time. But in nearly two full seasons thereafter, he would feature in just 11 more matches for us. Loaned to Watford for a few months in 1995, the midfielder moved to Reading on a permanent deal in February 1996. He also turned out for the likes of Notts County, Bristol City, Peterborough United and the now-defunct Rushden & Diamonds before embarking on coaching roles at Ilkeston Town, Gateshead, Wrexham and York City.

Casting your mind back nearly 33 years to your first Spurs start against Everton. What memories do you have from that day?

Darren: "I found out the previous day that I’d be starting. I was over the moon to be making my full debut… there were some nerves as well. But once the game started, it was crazy, all those nerves went and it was just like playing a ‘normal’ game of football. You just got on with the game."

Can you describe your winning goal?

Darren: "We were 2-1 down quite late on in the game. I think Darren Anderton got a goal back for us to make it 2-2. We were all thinking it was going to end that way. But we broke away again, down the left-hand side. I remember trying to catch up with play and I ended up in the situation where the ball arrived with me in the penalty area. I was about to blast it, but at the last second, I decided to side-foot it instead. There were a lot of Everton players on the line and I think I had an element of luck in that my shot just went in between them and into the far corner. If I’d have blasted it, there’s every chance it might have just hit someone on the line. Seeing it go in was obviously an incredible feeling. I think Everton kicked-off after the goal and then that was the end of the game!"

You must have been really pleased with your level of involvement in the first team during the 1993/94 season?

Darren: "Yes, it was what every young kid wants. You want to break into the team and then play regularly. Playing that number of games in my first season, I was probably thinking I was going to be at Spurs for my entire career. You tend to think like that when you’re young."

Who were the senior pros at the Club who helped you most in making the step up from our youth team into the first team?

Darren: "I was quite close to Teddy Sheringham. He was really good with me. We’d stay after training doing shooting practice, that kind of thing. There were some great pros at Spurs at the time… Gary Mabbutt was one. Everyone knows what a tremendous person he is. All the senior pros were great though. It was also nice breaking through into the team with players I knew from my two years at Lilleshall, Nick Barmby and Sol Campbell. We had a number of other youth team players break through and play for the first team… Jeff Minton, Kevin Watson, Andy Turner, Stuart Nethercott. It was good seeing that number of young players get their opportunity."

What was Ossie Ardiles like as a manager for you?

Darren: "Ossie was great for me. He obviously gave me my debut. He was a manager who let you go out and express yourself. It’s fair to say he put a bit more emphasis on the attacking side of things rather than defensively, hence we’d have 3-2 games, 4-3 games etc!"

Going back to the start of your Spurs career. How did you come to join us as a youngster?

Darren: "My story is similar to most young players. I was spotted playing for my local team in Romford… I can’t even remember the team name now! I was eight or nine when I was first invited to come up to Spurs to train once or twice a week in the ball court at White Hart Lane. When I was a bit older, at 13, I was invited to Lilleshall School of Excellence. I was still on Spurs’ books but when you go to Lilleshall, you’re there for two years. After that, I signed as an apprentice with Spurs at the age of 15 or 16. I was at Lilleshall with Nick and Sol. When we left there, Nick came and lived with me at my parents’ house in Essex and we’d travel up to Spurs together when we were first year apprentices. Myself, Nick and Sol all got into the first team relatively early on. We got our own independence then, Nick went and got his own house, so did I. You had to start growing up then!"

What were your experiences like playing for England at youth level?

Darren: "They were great times. I was captain of the Under-18s when we won the European Championships in 1993. I scored the winning goal – a penalty – in the final against Turkey at Nottingham Forest’s ground. I had captained another England age group at the European Championships and World Cup. And then, because of how my birthday fell, Ted Powell, who was managing the 18s at the time told me I was eligible to play in the Under-18s Euros and invited me to play at that tournament. And what an experience it was, going on to win it. We had an incredible team at the time with the Manchester United boys… Gary Neville, Paul Scholes, Nicky Butt, Chris Casper etc. There was Robbie Fowler and Julian Joachim. And obviously myself, Sol and Chris Day from Spurs."

In the summer of 1994, what was it like discovering we’d signed Jürgen Klinsmann?

Darren: "It was incredible. Jürgen was a great guy as well as a phenomenal player. It was an exciting summer for us. We brought in a number of players who had done well at that summer’s World Cup… Ilie Dumitrescu and Gica Popescu, who were really good for Romania. Us young players had been watching those players on the TV, so it was exciting times for them to become our team-mates."

We got some memorable results in the FA Cup during the 1994/95 season, winning 4-1 at Sunderland in the fourth round, triumphing 6-2 after extra-time at Southampton in a fifth round replay and winning 2-1 at Liverpool in the quarter-finals before a painful 4-1 defeat to Everton in the semi-finals…

Darren: "That’s right. We got that amazing result at Anfield and you did start to dream that it could be your year with a win like that. We played Everton in the semi-finals as you say and I was hoping to be involved in that one. But (then-manager) Gerry Francis chose to play Stuart Nethercott instead and I didn’t get on the bench either. It was disappointing to miss out on such a big occasion and it ended up being a hard day with the result."

What were the reasons behind your departure from Spurs in February, 1996?

Darren: "One of my last games for Spurs came in a 4-1 win over Manchester United (1 January, 1996) when I started in midfield alongside Sol as we had injury problems at the time, so I was brought into the starting XI and Sol played out of position. After that game, when our players were back from injury, I was dropped straight away, so I went to see Gerry. He actually offered me a contract to stay at Spurs. But, in the same breath, he was honest with me and said when his senior internationals were all fit and available, I was likely to be on the bench. I appreciated Gerry’s honesty and it was around that time that I decided I needed to move on. I really got the taste for playing in my first season in the first team. I just wanted to play more and more. But the following season was difficult for me in terms of the lack of starts and the same the season after. I started to get a bit frustrated then and eventually I left Spurs. I look back in hindsight and think maybe I should have stayed. I remember Darren Anderton having injury problems in the first season I’d left the Club (1996/97) and I think if I’d stayed, maybe I could have played more often. You never know though do you? I had to make a decision at the time and I wanted to be starting matches, it was as simple as that. I look back so fondly on my time at Spurs, from the age of nine all the way up to 22, when I left."

Fast forwarding in your career, what have you been up to since retiring from playing?

Darren: "I went into coaching after my playing days were over. I worked under Gary Mills, the ex-Nottingham Forest player, at Gateshead, then Wrexham and then York. We won the FA Trophy at York. I still live in North Yorkshire. I run a leisure park called Stonebridge Lakes nowadays. We’ve got fishing lakes, a caravan park, log cabins. I’ve got a 16-year-old daughter who has cerebral palsy, so she needs quite a lot of care. So, it works well for me to be here on the leisure park site to run a business and also be here to look after my daughter and be with my family."

And we understand you continue to follow Spurs?

Darren: "Yes indeed! I went to the Forest away game last weekend. I went to a few games last season, including going to the new stadium for the first time for the game against Burnley on the opening weekend of the season. The stadium was amazing. It’s quite incredible seeing it on the site of the old White Hart Lane. It’s certainly a bit different to the ground I knew when I was a player!"

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SPURSPLAY

Jamie Carr’s side have been in blistering form in front of goal so far in 2026/27, scoring 24 goals in four Under-18 Premier League game to rocket to the top of the fledgling standings.

We’re the only team in the division to have won all of our games so far, but we now go to Motspur Park for what is always a big test against our London rivals.

The Cottagers, for their part, have won three and drawn one of their four league games to date, with an intriguing top-of-the-table clash in prospect.

As he continues to mould his squad together, Roberto is asking the team to raise their levels again as we move onto matchday four of the new Premier League season.

It goes without saying that it has been a slow start to the 2026/27 campaign for us as we continue to search for our first win, but our Head Coach is seeing progress in the group.

Now, with the Toffees making the trip to Tottenham Hotspur Stadium, the Italian wants his players to take the game to David Moyes' side from the off, demanding that they play with courage and show the passion, bravery and qualities they all possess to ignite the noise in N17.

"I would like to see my players playing with courage, with personality, with energy - what we are doing on the pitch on the training ground," he said as he spoke to the SPURSPLAY cameras on Friday.

"I would like the players start the game, the first 10 minutes, with energy to deserve the support of the fans, I can say I know this stadium, especially after last season, the last games with me in my time, they were fantastic in our stadium.

"And now, I think they are waiting for a signal from us. And for that, I would like to start the game with personality, with energy, with pressure, with qualities to bring them inside of the pitch."

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SPURSPLAY

Wayne Burnett's team have clocked up the miles this week - a midweek trek to Exeter in the EFL Trophy followed by this trip up the M1 to Long Eaton.

If there were any physical effects of the mileage it didn't show at Grange Park as we flew out of the traps at the start of both halves - Reiss Elliott-Parris scored after two minutes, a feat repeated by Ellis Lehane after the break. In-between, Tyrese Hall finished clinically with Zach Marsh replying for the Rams.

The first half couldn't have started better as Miracle Adewole's cross was cleared to Elliott-Parris, who guided home a precise finish, side foot, along the ground into the corner from the edge of the box.

However, Derby responded almost immediately as Charlie Smith's low cross was turned home by Marsh from six yards.

We controlled the next half-hour, pinning the home side in their half with some lovely passages of attacking play and crisp passing, the returning Callum Olusesi key to it floating around in the '10' area. Tye Hall headed wide and Harry Byrne's shot was spilled by Alfie Halliwell, who did well to get up quickly and block Olusesi's follow up before Adewole fired over.

It felt like a goal was coming and it duly arrived on 28 minutes as Tye Hall went wide to Adewole, Tristan Gill directed his clearance straight to Tyrese Hall who rifled into the roof of the net for his third goal in as many league games this term. Halliwell then twice denied Olusesi.

Derby got back into it via a couple of counter-attacks, Gill and Dantel Hodges missed the target and Charlie Smith struck the crossbar from a free-kick, Sam Archer there to palm away Hodges' follow-up. Archer then had to be on his toes to parry away Marsh's strike from 20 yards.

We came out with some intent at the start of the second half. Tye Hall let fly within 30 seconds, then forced a fine save from Halliwell seconds later. A minute after that, substitute Lehane's curler from the left corner of the box was deflected home for 3-1.

It was another 15 minutes until the next action of note as Archer got his angles right to block from Cameron Wilson. Israel Green then headed over from close range.

We maintained a level of control after that, but clear-cut chances were at a premium, Johnson Osong going closest for the Rams with a curler just wide.

‘We didn’t maintain the standards’

Although we’d secured the three points, coach Wayne was unhappy with elements of what he saw, telling SPURSPLAY: “In the first half, for 80 per cent of the half we were very good but you can’t have such a wide spectrum and be 80 per cent very good and 20 per cent not so good. We didn’t maintain those standards in the second half and I’m very disappointed with the performance in the second half. Of course, I’m pleased we’ve won, but I’m disappointed in the second-half performance.

“The performance is very important, the way in which we play and the manner in which we conduct ourselves is extremely important and I didn’t think we maintained those standards and maintained those behaviours as well as we did in the first half. There was still some improvement in the first half needed but we weren’t anywhere near where we should be in the second half for sure.

“(In the first half) we played some really nice football, got in some really nice positions and created some really good chances but there were times in the first half where we were in control and unnecessarily gave the ball away and caused our own problems. As I said, for 80 per cent of the first half we were very good, some of our football was outstanding but for 20 per cent it was way below standard and you can’t have that disparity.”

Line-ups

Derby County: Halliwell, Gill (Gordon 59), Robinson, Cononville (Osayande 46), Offor (c), Tola, Smith, Hodges (McAndrew 59), Marsh (Green 59), Wilson, Jones (Osong 59). Substitutes (not used): Kane, Wren.

Spurs: Archer, Feeney, Sowunmi, Hardy (c) (Adedeji 86), Dorrington, Byrne, Adewole, Tye Hall (Moncur 77), Tyrese Hall, Olusesi (Lehane 46), Elliott-Parris (Ramsey 74). Substitutes (not used): Doran, Thomas.

Match data

Goals: Derby - Marsh 5; Spurs - Elliot-Parris 2, Tyrese Hall 28, Lehane 47.

Yellow cards: Derby - Smith 53, Tola 77; Spurs - Moncur 79.

Referee: Gareth Thomas.

Venue: Grange Park, Long Eaton United FC.

Weather: Mild, 18 degrees at kick-off.

Attendance: 310.

Speaking to SPURSPLAY to look ahead to our latest match at Tottenham Hotspur Stadium, the Head Coach revealed that World Cup winner Pedro had “felt a small muscular problem” and said he doesn’t want to risk the long-term fitness of both the right-back and also left-back Destiny, who has had injury problems over his own in 2026.

“Pedro Porro felt a small muscular problem, we have to see tomorrow if he’s available or not but in this moment I don’t want to take any risks. The same (with) Udogie,” Roberto said.

“Pedro Porro and Udogie are similar players because one, Pedro played a World Cup, a long World Cup and we already knew after the World Cup it could be a difficult management for him and for Udogie, last season (he) suffered many injuries, he played 60 minutes in Nottingham and we have to manage also Destiny in the best way we can.”

The boss confirmed at his pre-match press conference on Friday that new loan signing Mykhailo Mudryk has suffered an ankle injury and is sidelined along with Dejan Kulusevski, Wilson Odobert and Xavi Simons.

James Maddison, however, is back in the frame after missing our last three matches with a shoulder problem.

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Here’s what he had to say...

What’s the latest team news?

Roberto: “Kulusevski is not working with us in the last week. Not a big problem, the normal problem when one player is out for a long time, like Mudryk. It was a stupid injury of Mudryk, and we hope he can be back as soon as possible. For him and for us, for him because he suffered too much and for us because we lost one player, an important player. He played 20 minutes, 15 minutes in Nottingham, he played well, but it's the normal process when one player doesn't play for a long time.”

Is Maddison back?

Roberto: “Maddison, yes. I'm happy when all my players are available. It's maybe a problem for me because my decisions are not easy, but I want to manage all players together.”

How impressed have you been with Lucas Bergvall after he signed a new contract?

Roberto: “I’m delighted for the extension of his contract. He’s working very well. It's difficult now because the competition, especially in his position – Tonali, Bentancur, Gallagher are all players of high level, but I think at the end of the season he will play part of the game, many games, I think, and then he has to improve. We have to help him to improve, and he has to work like he has done, like he’s doing, especially in this season. At the beginning of the pre-season he has been fantastic on the pitch.”

How different is this squad compared to the game against Everton at the end of last season?

Roberto: “I think we are better than last season, especially the end of the season, many, many injuries. It's difficult to believe right now because we are not winning, we are not scoring, but I'm positive because I believe in my players, I believe in this group of players. I think the players have big, big qualities, big potential and now I'm positive. I don't say nothing more because at the end, there is always the result of the pitch and the performance, but I think we are working well also this week. In Nottingham, I watched something different than Brentford, for sure. Newcastle was a particular game because, until one hour of the game, I think we deserved to win that part of the game. Then we lost 2-0, but I think we are in the right way, in the right moment for the improvement.”

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Does the fact that the team is yet to score a goal play on your mind?

Roberto: “I'm not happy, for sure, because I suffer the defeat, I suffer when I don't score, but I'm not so young, I have experience enough to analyse better the situation. And I said in Brentford we were not ready for many, many reasons. In Newcastle, until the first goal, we played better than Newcastle and we deserved to score in the first half. Not one time, more times. In Nottingham we played a normal Premier League game against one physical team, one team who played the second ball. I think we didn’t concede a shot on our goal, we had one clear chance with Micky van de Ven on set-pieces and two big, big potentials, one was Tonali for Savio in the first half and in the second half, Marmoush for Kudus and Andy Robertson, so I think it was a normal game. We can play much better, for sure. We are not happy. Pressure, no. Why pressure? The pressure was last season in that situation of the table, not now, because now we are working to become a team and we are building a new team with new relationships, with new connections, with new style of play, with new, many players. So I think we have to stay calm and to stay positive and without any pressure.”

What do you expect from the new signings?

Roberto: “The qualities, for sure, because I am sure about the qualities of Robertson, Senesi, Mateus Fernandes, Tonali, Savio, JP van Hecke, Marmoush. I am sure. Even if they don't play well, I can't change my idea now. And then I would like to see one team playing with courage, with energy, to try to dominate the game, dominate the pressure with the right spirit, with the spirit I like.”

What do you expect from Everton?

Roberto: “Playing against Everton is the same, because Tarkowski, Branthwaite, Pickford, Dewsbury-Hall, all of them, Mykolenko, Grealish, are very good players, very physical players. They know very well the Premier League, but I think we have to be focused on our qualities, we have to be focused on what we have to do on the pitch and play without thinking about other things in the head.”

Do you need to win on Saturday to stop people talking about another possible season of struggle?

Roberto: “We need to win, we need to score, we need to win against Liverpool on Tuesday, against Aston Villa next week. We need to win, but it's not enough to say we need to win the game, we have to build the right way to win the game, so we have to press, we have to play, we have to keep the ball, we have to play with courage, to play following what we are doing on the training ground and then we go to see the result. But without this part of football, it's not like you win the game.”

You’ve mentioned the word courage twice…

Roberto: “Yes, because I think we could play much better because I work with the players every day, I know the players better than you, and during the week we play with more confidence, with more courage, with more freedom. And during the game when we have the opponent 3m, 4m, it's like we don't want the ball or we don't want to take any risks because if we lose the ball, we can concede a goal, what is the problem? I'm the coach, I take the responsibility I have to take without problem, but I would like to play, to play, to play, to play, to run, to press, to dribble, to shoot many times, more times on the goal, because I know the potential of my players.”

You mentioned after the Newcastle game about mentality…

Roberto: “No, after the first goal, because we played well, not amazing, but we played very well until the goal we conceded and then I saw a little demoralisation, a little down in the mood and I don't want that, because the game, if you concede a goal, 60 minutes, you have another 30 minutes to score one or two or three goals, and we have to push until the end. Also because, especially in this moment, we have to build our value, and we lose the game when the referee says it's finished, the game. Until the end of the game, we have to push, forgetting the result, because it's our job. We play for a big club, and we have to respect our club. How? Pushing until the end. When the game finishes, we go home and we go to see if we won or we lost the game. For that, I said the mentality, not in general. In general, I'm happy because I can't say anything about the mentality, the spirit, the behaviour of the players. Nothing to say.”

What happened with Mudryk’s injury?

Roberto: “Playing without tackle, without different movement, he felt pain (in the) ankle and then after two days he made the medical check and we knew the problem, but after a long time, we knew. A stupid injury, but we are not stupid. When we signed Mudryk, we already knew it could be difficult to come back as a normal player.”

Is Kudus ready to start and how important is he?

Roberto: “I think very close to being ready to start the game. It’s an amazing feeling for me. I wanted Mo Kudus when I was in Brighton. I pushed a lot to bring him before he went to West Ham. He can play as a winger, as a number 10 and as a striker also, and he is an amazing player.”

Do you see Savio as being able to play on the left?

Roberto: “I was a player and I was a winger or maybe more number 10, but I played many years as a right-winger and left foot. I love the wingers on the opposite side but Savio is top. I think he can play in both positions.”

Can Maddison play on the left as well?

Roberto: “Yes, I think he can be an option. Normally he is not a winger but we have to build the situation to put inside and push higher the left-back. Maddison is very smart and when you play with smart players, they can understand the right position, they can smell the right position. It depends on the situation but it can be a good solution and especially because Conor Gallagher and Mateus Fernandes as a 10, they can play as a midfielder, as a 10 midfielder, not as a winger inside like Xavi Simons last season. Maybe sometimes you have a midfielder who is able to start as a winger and then come inside with the ball in possession, but it is not like this for me and my idea for Gallagher and Mateus. But yes, Maddison is like Xavi and he can play that position.”

Would you like to see Archie Gray sign a new deal like Lucas Bergvall just has?

Roberto: “I am happy when… I am generous as a man and when the people close to me extend their contract, I am happy.”

What’s the latest with Richarlison?

Roberto: “I don’t know, I don’t know. It’s not my job. What I can say is I know very well what the club has done for Richarlison and I know very well what Richarlison has done for the club in the last month, in the last two months. I know, the club knows, he knows, his agent knows, everyone knows. Better than you (the media). Much better.”

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Midfielder Madders hasn’t been involved since picking up a slight shoulder issue in our opening-day defeat at Brentford – missing our last three matches in all competitions as a result – while forward Mo has made second-half substitute appearances in our last two games, his first action since January in the wake of a hamstring injury.

After confirming to reporters that Madders is back at his disposal during his press conference ahead of Saturday’s clash with Everton at Tottenham Hotspur Stadium (5.30pm UK), Head Coach Roberto reiterated his long-term admiration of Mo and said that the Ghana international continues to make progress.

“I think (he’s) very close to being ready to start a game,” he said. “It’s an amazing feeling for me. I wanted Mo Kudus when I was in Brighton, I pushed a lot to bring him before he went to West Ham. He can play as a winger, as a number 10, as a striker up front and he’s an amazing player.”

Roberto also confirmed that Mykhailo Mudryk has been ruled out with an ankle injury in the wake of his debut at Nottingham Forest last week – his first competitive action in some 20 months. He joins Dejan Kulusevski, Wilson Odobert and Xavi Simons on the sidelines.”

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A deadline day loan arrival from Chelsea, the winger played his first competitive minutes in 20 months when he came on for his debut during the second half of last weekend’s goalless draw at Nottingham Forest.

But after subsequently picking up an ankle issue, he’s now been ruled out of action and will miss Saturday’s clash with Everton at Tottenham Hotspur Stadium (5.30pm BST).

“It was a stupid injury for Mudryk and we hope he can be back soon as possible, for him and for us,” said Roberto at Friday’s pre-match press conference. “For him because he has suffered too much and for us because we have lost one player, an important player.

“He played 20 minutes in Nottingham, he played well, but it's a normal process when a player has not played for a long time.”

Pressed on what happened, the Head Coach continued: “He felt pain in the ankle. Then after two days he made the medical check and we knew the problem. But after a long time (not playing), we knew (that this could happen). A stupid injury, but we are not stupid. When we signed Mudryk, we already knew it would be difficult for him to come back as a normal player.”

Roberto also confirmed that long-term absentee Dejan Kulusevski has not trained with the team in recent days: “Kulusevski is not working with us in the last week,” he added. “It’s not a big problem, it’s a normal problem when one player is out for a long time, like Mudryk.”

Kulusevski remains out along with Wilson Odobert and Xavi Simons.

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