The York Press

Hosting Northampton Town at the LNER Community Stadium this Saturday, York enter the FA Cup at the first round looking to progress past their fellow League Two side.

It's a competition which City haven't seen much success in in recent years - with a second round tie against Wigan Athletic being the furthest they have reached in the last 16 years.

But the Minstermen have plenty of good times to look back upon.

Here's our pick - and videos - of some of York's greatest home ties in the FA Cup.

York City 3-1 Tottenham Hotspur - 1955

Those who can remember this incredible Bootham Crescent meeting will look back upon it with great fondness.

A crowd of 21,000 people packed into the ground to watch York topple First Division Spurs, in an FA Cup run that saw City go all the way to the semi-finals.

They had trailed to Tottenham, with George Robb putting the visitors ahead.

But a magnificent effort from the Minstermen saw them turn the tie on its head - with goals from Norman Wilkinson and Billy Fenton putting York in front, before Wilkinson steered in Fenton's cross for the third.

After the game, Spurs' Danny Blanchflower said: "York's standard of play left us speechless."

York City 0-0 Huddersfield Town - March 1938

A goalless draw might be looked upon with disappointment, but this was a record-breaking afternoon for City.

Hosting another Yorkshire side in Huddersfield, the Minstermen marked their record attendance at Bootham Crescent, with an incredible 28, 123 supporters through the turnstiles.

York did come close to a winner as Peter Spooner had a late header cleared off of the line, but instead settled for a replay, where they lost 2-1 in West Yorkshire.

York City 1-0 Arsenal - January 1985

Up there with one of City's greatest-ever giant-killings was when the Minstermen stunned the footballing world to beat Arsenal at Bootham Crescent.

Hosting top flight Arsenal, Keith Houchen's penalty was enough to fire York into the fifth round of the FA Cup - earning a tie with another giant in Liverpool.

The Arsenal team consisted of eight internationals and had cost more than £4.5 million to assemble - a huge fee back then - but they couldn't break down City's squad at a snowy Bootham Crescent.

York City 1-1 Liverpool - February 1985

One month on from their Arsenal heroics, York came so, so close to taking the scalp of another footballing giant.

They would go on to lose a replay to Liverpool 7-0, but City succeeded at Bootham Crescent in holding their star-studded visitors to a draw.

With players like Ian Rush and Kenny Dalglish arriving to North Yorkshire, it was the heart of York that managed to earn the replay.

Ricky Sbragia levelled the scores after Rush's opener in another fantastic FA Cup clash.

York City 3-3 Southampton - January 1971

In 1971, this was a huge David vs Goliah meeting as Division Four York welcomed First Division Southampton to Bootham Crescent.

A goalless opening 45 exploded into life in the second-half, as the Saints broke the deadlock with Jimmy Gabriel heading past City goalkeeper Ron Hillyard.

Mick Channon, an England international, then doubled Southampton's advantage with 12 to go and it looked to be over for York.

They showed fight as Kevin McMahon halved the deficit just two minutes later, but a quick response from Southampton saw their two goal lead restored as Ron Davies bagged a third.

City weren't done though - Dick Hewitt first fired home to make it 3-2 with three minutes to left, and with a minute to go, Paul Aimson found the inside of the post to earn a dramatic replay.

Spurs have spent the majority of this week in a warm weather training camp in Marbella, but Savio was absent after he reported a “muscular problem” on Tuesday and Bergvall is sidelined for “two weeks” with a knee issue.

Those absences along with Kulusevski’s ever-improving fitness have opened the door for the Swedish playmaker to potentially play on Monday night after a serious knee injury has sidelined the attacker since the end of the 2024-25 season.

“Yes, Kulusevski on the bench. We had a meeting with the medical staff. They gave the OK and it’s great news. I think it’s one of the best news after Everton game last season because Deki he suffered too much. He deserves to feel emotion on the pitch,” boss Roberto De Zerbi told a press conference.

“Unfortunately Savio on Tuesday… before we leave for Marbella, he felt a muscular problem. We lost him for some weeks unfortunately.

“And Lucas Bergvall because he had a problem at the beginning of the game in Manchester.

“The day after Manchester (United), Sunday, he came to (the) training ground to our medical staff. And I think two weeks (out).”

De Zerbi provided a positive update on right-back Pedro Porro, who could be available for the trip to Chelsea next Saturday.

However, bottom-of-the-table Spurs will be missing seven players for the clash with Coventry with Rodrigo Bentancur suspended for a fixture where the hosts will be desperate to end a six-match winless start to the new Premier League campaign.

“Coventry is a good team. They played a fantastic Championship last season,” De Zerbi said.

“But we are Tottenham, keeping humility, keeping what you want, but we want to show to be good enough to win the games, especially if we deserve to win the games.”

Kulusevski could be required to help Spurs get off the mark in the league after a torrid spell on the sidelines with a patella injury, which required a second procedure in March to fix the long-standing problem.

After Kulusevski missed Tottenham’s Europa League triumph in 2025, the whole of last season and this summer’s World Cup, De Zerbi was delighted to tell the 26-year-old on Saturday that he would be in the matchday squad against Coventry.

De Zerbi revealed: “ I said to him, ‘I spoke with the medical staff and they gave me the OK’ and he smiled like this (wide).

“And we are happy. We are very, very happy. It’s not football. I’m not speaking about football. OK, he’s a special player, but we are speaking about different things. He suffered a lot and his reaction was great.”

Richarlison remains unavailable after he was left out of Tottenham’s 25-man Premier League squad following an eventful end to the summer transfer window – but featured and scored for the club’s Under-21s on Tuesday in a Jersey Mike’s Trophy match at Cheltenham.

On Saturday, Richarlison posted on his Instagram story “you are right” alongside a story where ex-Everton forward Duncan Ferguson criticised De Zerbi’s treatment of the Brazil forward.

But De Zerbi insisted: “It’s not my problem any more. You have to ask Vinai (Venkatesham), to Johan (Lange), it’s not my problem.”

Spurs remain winless in the Premier League after six matches, but produced an impressive display in Saturday’s 1-1 draw at Manchester United – where Maddison was used off the bench for a fifth time this season.

The 29-year-old has struggled to get back to full fitness after two serious knee injuries in 2025, including a rupture of his anterior cruciate ligament, but Stevens, who was academy manager during Maddison’s time at Sky Blues, believes the playmaker can become Tottenham’s difference-maker again.

Ahead of Coventry’s trip to Spurs on Monday, Stevens told the Press Association: “His driver is, ‘am I playing 90 minutes and can I go and score some goals and ignite the fans,’ you know? So this injury would have hurt him a lot.

“Even in a 10-minute spell (now), when he comes on, he takes the ball and he makes things happen.

“He makes things tick and he gets the team playing forwards. He gets the team moving up the pitch.

“And good grief, Tottenham have had a tough time. They’re an unbelievable football club and you know the players they have, maybe he’s the bit that’s going to connect everything together.

“I hope he’s going to return and he’s going to connect everything together for Tottenham because I think he has that ability to do that.”

Stevens watched 52 youth prospects make their full debut for Coventry during 12 years in charge of the academy and can remember how a young Maddison “ran that group” to ensure certain standards were met.

Coventry’s financial plight more than a decade ago opened the door to youth-teamers and despite being sent off in his 12th appearance, Maddison grasped his chance and scored in a final day win at Crawley which kept his boyhood club in League One. Four years later and he had played for England.

Tottenham were interested in Maddison in 2016, but had to wait another seven years to secure his services and a rollercoaster spell in N17 has followed of 83 appearances, one Europa League triumph and a nervy relegation battle.

Ahead of Maddison’s third meeting with Coventry, Stevens can still recall the diminutive midfielder that caught the eye on his first day.

“James was under-11. We were away at MK Dons and there was this pitch behind me and there’s this little fella who just kind of carried the ball and twisted and turned,” Stevens said.

“We knew he was a good player. Every team we ever played against were always aware of him and they knew him. And, I’ve said it many times, he just loved football.

“Loved football, obsessed with it and no surprise he has had the career he’s had.

“If you see those pictures of that 2014-15 season, he does look like a boy, but he might have been a boy in his body, but he certainly wasn’t a boy in his mentality, in his understanding of the game and his courage.

“That goal at Crawley that year, the club were 20 minutes away from a pending relegation. And I remember he arrives in the penalty area and he punches one bottom corner.

“Local boy, lives 300 yards from the academy training ground… you couldn’t have wrote a more apt script really.”

Coventry fans only enjoyed Maddison for 42 appearances, but he can expect a special reception on Monday.

“He hasn’t changed,” West Brom academy boss Stevens insisted.

“He came into his box after a game (in 2024), jumped over the sofa and we’d not seen each other for two or three years. And it was like he’d never been away.

“You don’t forget that. That’s a boy that is really appreciative of all the things that staff of Coventry did for him.

“Everybody’s really proud and Coventry will be proud as well. They’ll be looking forward to playing against him, I’m sure.”

Kulusevski has not played for Spurs in more than 500 days following a serious knee injury, but featured in a behind-closed-doors match during the international break and will travel to Old Trafford to offer support.

With Kulusevski inching closer to an emotional return after multiple setbacks and fears he may never play again, De Zerbi used the Swedish attacker as a reference point for bottom-of-the-table Tottenham, who have taken two points from their first five Premier League fixtures.

“Yes, he’s an inspiration. He reacted very well, with character, with courage, with passion. Yes, passion. It’s a good word, passion. We have to take inspiration from Deki. I said the same in the meeting to the players,” De Zerbi said.

“Tomorrow he comes with us, also (Pedro) Porro (for support). I want all players tonight and tomorrow, but he is working very well. I think he is an example for everyone, Dejan Kulusevski.

“Forget the player, but the example of how he reacted to the injury, the reaction to being unlucky, the character he showed this time, was an example, a reference for everyone.”

Quizzed on when he could make his long-awaited return, De Zerbi explained: “I don’t know, it’s not just my responsibility.

“We are working together with the medical staff. They are working very well with him, they have done special work. We have to analyse week by week.”

Spurs have sorely missed the creativity and character of Kulusevski during his 17-month absence, but De Zerbi is calm after a slow start to the campaign and was reminded of a similar situation for Aston Villa last season.

Asked about Villa being able to finish fourth after they went five games without a win, De Zerbi said: “Yes, it’s possible. Why not? But to do what Villa did, we have to click.

“I think the first win is not a gift from God. You have to deserve to win. And we didn’t deserve to win so far.”

James Maddison will travel to Old Trafford and is available but De Zerbi hinted only for a cameo role after he missed days of training over the last week.

With Kulusevski still absent and Maddison not back to his best, it has increased calls for Spurs’ highly rated 18-year-old Luca Williams-Barnett to get an opportunity.

Major clubs across the world are circling playmaker Williams-Barnett, but Spurs have opened talks with the mercurial talent over a new deal, the Press Association understands.

De Zerbi acknowledged he was “thinking” about when to include Williams-Barnett in the squad after he made his second Tottenham appearance late on in the Carabao Cup win over Charlton.

The boss said: “Special talent, special personality also because he’s arrogant, but arrogant good for football.

“You have to believe in yourself. Not forgetting to be humble. Anyway, humility but believe in yourself and the right example is Luca.”

Kulusevski has not featured in a competitive fixture for more than 500 days after an issue described as a knock at the end of the 2024-25 campaign turned into a knee problem which put his career in jeopardy.

However, with Kulusevski able to resume full training again last month, the Press Association understands the Sweden international has recently taken part in an 11-v-11 match for Spurs against an academy XI at the club’s Hotspur Way training ground.

This is the latest positive development for the 26-year-old on a long road to recovery and pushes him closer towards a place again in Tottenham’s matchday squad, which could even occur at Manchester United on Saturday.

Boss Roberto De Zerbi admitted Kulusevski’s return would be like a “new signing” three weeks ago but made clear the club must “manage Deki in the best way we can” after a 17-month absence.

A fresh update on Kulusevski’s availability will be provided by De Zerbi at Friday’s press conference.

An innocuous clash of knees with Marc Guehi during a 2-0 loss to Crystal Palace on May 11, 2025 started Kulusevski’s injury nightmare.

The initial concern was whether the versatile attacker would make the club’s Europa League final but the immediate description of “just a knock” by Ange Postecoglou, the Spurs boss at the time, after a brief chat with medical staff proved wide of the mark.

A patella issue in Kulusevski’s right knee was discovered and he underwent surgery soon after but hopes of a return during the opening months of the 2025-26 season were wiped out when his injury was labelled a “longer one” by Postecoglou’s replacement Thomas Frank.

Frank later stated there was a “good chance” that Kulusevski would return by the end of 2025 but with pain still present, the next course of action was an injection at the end of December which failed to have the desired effect.

Described as a “complicated injury” by Frank on January 8, he suggested a timeline for Kulusevski would be more clear once the knee had “settled” weeks after the injection.

Yet, with Kulusevski still no closer to a return, an appointment with a knee specialist in February acted as the catalyst for light at the end of the tunnel with a crucial minor arthroscopic procedure undertaken in March.

Kulusevski said at the time on Instagram: “It was really positive that I did this little procedure and that we were able to find the problem. Now everything should be solved.”

Kulusevski’s first full training session with Tottenham in almost 16 months occurred at the end of August and although he was then taken out of action for a small period, he resumed work with De Zerbi’s squad again last month.

After Kulusevski played his first match in 17 months during this international break, all eyes are on if he will join Spurs at Old Trafford.

It has been more than 500 days since Kulusevski last played competitively at the end of the 2024-25 campaign after an innocuous challenge in a 2-0 defeat to Crystal Palace resulted in a troublesome patella injury in the right knee of the Swedish attacker.

A lengthy absence affected by multiple setbacks has followed, but Kulusevski has returned to first-team training and will target a positive end to a difficult journey with a potential comeback for Spurs during October after the ongoing international break.

Compatriot Bergvall told Swedish media outlet Fotbollskanalen: “He is incredibly hungry and has done incredibly well. He is a real machine. We are all looking forward to having him back.

“I absolutely think so (soon). Then it’s difficult for me to judge how he feels and how the club sees it, but it’s clear that he’s doing incredibly well in training and is making strides every day.”

Asked what it would mean for Kulusevski to play for Sweden again after he visited Graham Potter’s national team in March before he missed this summer’s World Cup, Bergvall said: “An incredible amount.”

Right-back Porro was set to enter the final two years of his previous deal this summer and despite a host of Europe’s biggest teams circling, the former Sporting Lisbon full-back has agreed a contract until the summer of 2031, the Press Association understands.

An option for a further 12 months is also included, PA understands, and is the latest key move made by Spurs under Roberto De Zerbi since they avoided relegation on the final day of the 2025-26 campaign.

De Zerbi said: “Pedro is a very important player for us, who has consistently shown his ability to influence matches in both defensive and attacking situations.

“As well as his technical quality, I also love his mentality. Every day he wants to work, to learn and to improve, and these are the characteristics that help players reach the highest level.

“He understands football in a very intelligent way, and brings energy, intensity and personality to the team.

“This new contract is good news for everyone at the club. We believe in Pedro, and I am excited to continue working with him and helping him achieve even more in the coming years.”

In a video posted by the north London club on Instagram, Porro said: “Hi Spurs fans. I’m so happy to sign a new contract. Can’t wait to see you next season. Come on you Spurs!”

Porro made 47 appearances during a dismal last season for Tottenham, which did end with survival, and the full-back impressed during De Zerbi’s seven-game tenure.

Signed for 45million euros (£39.5m) in 2023, the Spain international has become one of the club’s most reliable players in terms of availability amid multiple injury crises in recent seasons.

The 25-year-old has produced 13 goals and 26 assists for Spurs and celebrated his 150th appearance in last month’s 1-1 draw with Leeds.

A new contract for Porro continues a busy start to the summer for Tottenham with free agents Andy Robertson and Marcos Senesi signed. Brighton’s Jan Paul van Hecke has also been targeted and two bids for the Dutch centre-back have been turned down, PA understands.

Brighton have turned attention to Spurs youngster Luka Vuskovic amid negotiations for Van Hecke but a £30m offer on Friday has been rejected.

Oliver Boast, who turned 17 last month, has agreed to sign a first professional contract with Premier League side Tottenham Hotspur.

The young forward was born in York, and first broke into academy football at Leeds United, signing for the Whites aged just nine.

Rising through the ranks at Leeds, Boast established himself as one of United's most exciting prospects, earning the attention of fellow Premier League clubs.

He landed at Tottenham Hotspur last July, ending an eight year association with Leeds and beginning a new chapter with Spurs.

In his first full season with Tottenham, Boast has recorded 14 goals and 4 assists in 27 matches in the under-18's Premier League,

That included a sensational performance against Birmingham City under-18's, in which Boast scored a hat-trick and got one assist in a 4-1 dismantling of the Brum.

In all competitions, Boast scored 17 in total when contributing to Tottenham's run in the Premier League under-18's Cup.

Boast's impressive displays over the years with Leeds and now Tottenham has also earned him a regular spot in the England under-17's side, with the young man from York representing his country.

Scottish outfit Hearts have reportedly had a £750,000 bid rejected for the defender as they face a battle with a number of League One sides, including Oxford United.

Fagan-Walcott had been part of the York City team that won the National League in dramatic fashion this season.

Fagan-Walcott began his career in Tottenham Hotspur’s academy and made his senior debut during a 3-0 Champions League defeat to RB Leipzig in the 2019/20 season. After a loan spell with Dundee, he joined Cardiff City following his release from Spurs.

Opportunities proved limited in South Wales, leading to further loan moves with Dunfermline Athletic and York City.

It was at York where the defender found his footing, doing enough to earn a permanent switch ahead of the 2025/26 campaign.

He went on to play a key role in York’s National League title-winning season, making 36 appearances as the club amassed 108 points to secure promotion back to the EFL.

Fagan-Walcott also made a significant impact in the final third, scoring eight goals and providing four assists from defence.

Fagan-Walcott was previously tight-lipped on his future, telling BBC York: "I don't actually know whose come in.

"I've spoken to my agent, but we're all on cloud nine at the minute and I don't know what's happening."

A year on from Europa League glory and Spurs’ first trophy in 17 years, the north London club face the prospect of a catastrophic first relegation since 1977 if they lose at home and 18th-placed West Ham get the better of Leeds.

The build-up to a seismic match in the history of Tottenham has been overshadowed by the controversial move of injured captain Cristian Romero to fly to Argentina to continue his rehabilitation from a knee issue ahead of the World Cup, but De Zerbi will not waste any energy on the topic.

He said: “I don’t want to answer about Romero, about (Dejan) Kulusevski.

“They can’t play, they don’t play and they are not here. My focus is on Djed Spence, on (Randal) Kolo Muani, on Richarlison.

“We have to play and to play with blood, with character and with spirit because it’s a final. They played a great final last season and they won a trophy.

“Maybe there was a bonus, no? After tomorrow, there is not a trophy, there is not a bonus, there is something more important than a trophy and a bonus, there is the future of the club.

“There is the history of the club, there is the pride of the players, there is the pride of the family of the players, there is the dignity of every one of us, and for that, I can’t lose energy thinking about the next season.”

Romero’s decision to go back to Argentina has sparked anger amongst the fanbase, but there will be support shown for those involved on Sunday with the team coach set to be welcomed to the stadium by thousands of Spurs fans.

De Zerbi was also happy to dish out praise to stand-in captain Micky van de Ven, he added: “I think he is the best centre back in the Premier League.

“We talk a lot of time because I think he suffered maybe too much for the situation of Tottenham this season. He’s a sensitive guy, he’s a good guy and in my time, I think he played amazing.

“And for that, I’d answer he’s the best centre back, left centre, in the Premier League.”

After Kolo Muani produced an abysmal display in a 2-1 loss at Chelsea on Tuesday, De Zerbi must ponder whether to give the Paris St Germain loanee one final chance, but he does have other options, including Spence after his a call-up to England’s World Cup squad.

“I love Djed as a guy,” De Zerbi reflected.

“He has a big heart, he is a big player and a big guy.

“Right wing we can play Kolo Muani, (Lucas) Bergvall, Souza like Liverpool game, we can play Djed Spence.

“We can play Mathys Tel in the right side and (James) Maddison on the left side, or Pape Sarr in the left side and Mathys Tel in the right side.

“We have to find the solution.”