Manchester United enjoyed three elite signings from Tottenham down the years, but there could have been a fourth player to add to that list if it weren’t for a missed opportunity by the Red Devils in 2023.
Although transfer negotiations tend to be notoriously difficult when it comes to Tottenham, Sir Alex Ferguson had a knack for taking great players from the north London outfit.
In 1997, Teddy Sheringham was signed for £3.5 million to replace the retired Eric Cantona.
Sheringham linked up with fellow forward Andy Cole, Dwight Yorke and Ole Gunnar Solskjaer and went on to win the Treble in 1999.
The best moment provided by the English striker was the 91st-minute equaliser and assist for the winner in the 1999 Champions League final against Bayern Munich.
Who is Manchester United’s best ever signing from Tottenham?
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Michael Carrick would make the same move as Sheringham in 2006, taking the 16 shirt from Roy Keane following a £18.6 million deal. He helped transition the United side and played a key role in the 2008 Champions League final.
A year on from Carrick’s arrival, Ferguson hijacked Man City’s attempts to sign a new striker on deadline day when he brought Dimitar Berbatov to Old Trafford. The Bulgarian went on to score 56 goals in 149 appearances.
Harry Kane playing for Bayern Munich
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Harry Kane could have joined prestigious Man Utd list
Tottenham have had many top players down the years, but none of them got away quite like Harry Kane.
Kane was heavily linked to United, especially in the summer of 2023, before he joined Bundesliga giants Bayern Munich.
The Red Devils were reportedly put off by the £100 million price tag, deeming it too expensive for the then 30-year-old.
Kane eventually moved to Bayern in a deal worth approximately £120 million. Since his switch to Germany, he has scored 121 goals in 128 games.
United opted to sign Rasmus Hojlund from Atalanta, but it doesn’t look like the Dane has a future at Old Trafford after being sent on loan to Napoli at the beginning of the 2025/26 season.
However, after watching Hojlund score just 26 goals in 95 games and needing to invest in another expensive striker last summer, United ended up spending more money and getting fewer goals in return.
Sesko may be a solid option long-term, but United would have enjoyed better results over the past three years had they signed Kane instead of Hojlund.
The 32-year-old is still scoring goals and would have been a potent force in the same team as Bryan Mbeumo and Matheus Cunha.
Kane has scored 36 goals in 32 games for Bayern this season.
Another ex-Tottenham player that got away from United was Luka Modric before he left and won everything at Real Madrid.
Man Utd HAVE to turn this record around vs Spurs this time…
Are you confident Michael Carrick will get a win?
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Who was the last Tottenham player to move to Man Utd?
Sergio Reguilon was the last Tottenham player to join United, albeit on loan.
The Spaniard came in as a short-term, emergency loan due to the lack of left-back options in the squad and Erik ten Hag’s unwillingness to play Alvaro Fernandez before he was sold to Benfica.
Reguilon’s loan deal was terminated after four months as he returned to Tottenham.
The 29-year-old is currently playing for MLS outfit Inter Miami.
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