Man Utd to launch transfer raid on fierce Premier League rivals for first time in 22 years

Manchester United could do incoming business to sign a Leeds United player for the first time since 2004, with reports that they are keen on bringing him to Old Trafford.

The rivalry between the clubs dates all the way back to the 1960s, when they were both fighting for First Division titles under Sir Matt Busby and Don Revie.

It is nicknamed the Roses rivalry given that United and Leeds are situated in Lancashire and Yorkshire.

Leeds won the 1991/92 First Division title in what was a straight fight with United, and a fixture between the two sides in 1997 ultimately served as the start of the infamous feud between Roy Keane and Alf-Inge Haaland.

Leeds were relegated from the top flight in 2004, having fallen into serious financial difficulties as a result of their significant spending during the late 1990s and early 2000s.

It took the Whites 16 years to return to the Premier League under Marcelo Bielsa, but their 2-1 win over United at Old Trafford this season shows the rivalry very much still means something.

That is why reports of United's latest transfer target come as something of a surprise.

According to talkSPORT, they want to bring goalkeeper Karl Darlow to Old Trafford.

Darlow, 35, is being eyed as a backup to Senne Lammens, with the fact he is also homegrown seen as a major reason behind United's pursuit.

The former Newcastle goalkeeper has often been second choice at Elland Road but replaced Lucas Perri between the sticks for Leeds midway through last season and made 22 Premier League appearances.

He is out of contract this summer but Leeds are attempting to extend his deal.

Karl Darlow made 22 appearances for Leeds during the 2025/26 season (Image: Getty)

During the second half of the campaign, Leeds conceded only 24 goals - compared to 32 during the first half of the season - and were eighth in the Premier League form table.

When was the last Leeds to Man Utd transfer?

The last time a player moved directly from Leeds to Manchester United was forward Alan Smith, who moved to Old Trafford for a fee of around £9 million following Leeds' relegation in 2004.

The deal was even more emotionally charged by the fact that Smith had come through Leeds' academy, and fans turned on him following the transfer.

He told Soccer AM in 2002 that he would 'never' sign for United, and kissed the Leeds badge on the day they were relegated from the Premier League.

Alan Smith scored on his final appearance as a Leeds player (Image: Getty)

The caveat was that Leeds were in desperate need to sell players after dropping down to the Championship due to their serious financial position.

They had borrowed heavily against future gate receipts and TV revenue during the late 1990s - which effectively made qualifying for Champions League football a priority in the years to come.

Leeds lost in the Championship play-off final in 2006 and entered administration the following season, before being relegated to League One.

Whether Darlow will face as much venom from Leeds supporters as Smith did - the stance of many has softened since - remains to be seen, but he could mark a 22-year first by moving to Old Trafford.