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!"
Choose your XI - play our Selector!