Eric Cantona - November 1992

Cantona's move to Man United was credited as one of Sir Alex Ferguson's most successful moves, with the Frenchman helping to transform his side into title winners.

The maverick star had seen his relationship break down with Leeds boss Howard Wilkinson leading to speculation over a departure.

Leeds chairman Bill Fotherby called his Man United counterpart Martin Edwards to enquire about signing Denis Irwin. After the suggestion was rebuffed by Edwards, Ferguson then asked about Cantona’s availability with a £1.2m deal then being struck.

While initially seen as a risky move, Cantona helped inspire Man United to a first title in 26 years. The Frenchman was part of four title winning sides at Old Trafford and won two FA Cups.

 Rio Ferdinand - July 2002

Ferdinand became the most expensive British footballer in history when he completed a £30m move in 2002 after two seasons at Leeds. Ferdinand has claimed he sat in the office of Leeds chairman Peter Ridsdale for six hours to force through the transfer.

The deal came amid growing concerns over Leeds financial situation, which was referenced by Sir Alex Ferguson when the transfer was completed.

‘A transfer like this has to be difficult. Leeds are a big club and our fiercest rivals, and he had four years left on his contract,’ Ferguson said. ‘We were hopeful because of Leeds' financial position. I think Peter Ridsdale has admitted that. Most importantly, Rio wanted to come here and this contributed to the deal.’

Ferdinand would go on to win six Premier League titles, the Champions League and two League Cups during his time with the Red Devils.

Alan Smith - May 2004

Life-long Leeds fan Smith moved to Old Trafford in a deal worth £7million, with Danny Pugh going the opposite way.

Smith opted to make the move following Leeds relegation to the Championship, which had left him in tears on the final day of the season. Smith's move angered Leeds fans having previously declared he would never play for Man United.

The move, however, had helped Leeds amid the club's financial turmoil with Smith also waving a fee that was owed to him.

Sir Alex Ferguson hailed Smith, stating 'I have never been more impressed with a young player, his desire to play for Manchester United is fantastic'.

Smith career at Man United was heavily impacted by a broken leg and dislocated ankle he suffered in an FA Cup tie against Liverpool. He ultimately played 93 times for Man United, scoring 12 times, before moving to Newcastle. 

Karl Darlow - July 2026

Darlow is the most recent player to move between the two clubs, with the goalkeeper rejected a new deal at Leeds in favour of a move to Old Trafford.

He had been Leeds first choice goalkeeper for much of last season but is now back-up to Senne Lammens at United. Darlow made his debut in Man United's Carabao Cup defeat by Brighton.

When his summer move was confirmed, Leeds issued a 309-word statement but declined to name where Darlow had moved, instead stating he 'wished to explore a different challenge'.