Roy Keane to Blackburn, 1993
Blackburn were on the verge of signing Keane following Nottingham Forest’s relegation, but manager Kenny Dalglish realised late on Friday afternoon that he hadn’t brought the correct forms and would have to wait until Monday to finalise the deal.
One phone call from Alex Ferguson was enough to convince the Irishman that a move to Manchester United would be best for his career. The two parties quickly reached an agreement, leaving Dalglish and Rovers furious.
Jimmy Floyd Hasselbaink to Barcelona, 2003
Barcelona have historically done well with Dutch players and Louis van Gaal wanted to continue that tradition by partnering Hasselbaink with compatriots Patrick Kluivert, Marc Overmars and Frank de Boer in Catalonia.
A transfer fee was agreed and the deal was set to go ahead until a 2-0 defeat by Celta Vigo saw Van Gaal lose his job – and Hasselbaink lose his hopes of a switch to the Camp Nou.
Demba Ba to Stoke, 2011
Tony Pulis desperately needed a goalscorer in 2011 and thought he had his man when Stoke agreed personal terms with Ba.
However, a medical flagged up knee problems that had previously scuppered a move to Stuttgart, causing the Potters to swiftly back out of the deal. It was the wrong decision – Ba ended up at West Ham and went on to score 50 goals in England for the Hammers, Newcastle and Chelsea.
Willian to Tottenham, 2013
Everything was in place for Willian to join Tottenham in the summer of 2013, but Chelsea decided to hijack the move with a late offer of their own.
The Brazilian was at Spurs' training ground when he learned that their London rivals had entered the race for his signature. Needless to say, Daniel Levy wasn't at all happy when Willian made his excuses and headed to Cobham to sign for the Blues instead.
Steven Gerrard to Chelsea, 2005
Chelsea did everything in their power to extract Gerrard from his beloved Liverpool, offering a huge contract and the promise of that long-awaited Premier League title.
The saga dominated summer 2005 after the darling of the Kop submitted a transfer request following the Reds’ Champions League triumph in Istanbul. A tearful farewell seemed inevitable, only for Gerrard to change his mind as the fans threatened to turn against him.
David de Gea to Real Madrid, 2015
De Gea was identified by Real Madrid as the man to succeed the legendary Iker Casillas, but negotiations between los Blancos and Manchester United were painfully slow.
Madrid finally looked to have snared their man on deadline day, but a problem with the paperwork saw the move collapse at the last minute. Four years on and De Gea remains a United player.
Daniel James to Leeds, 2019
James was a wanted man in January, and Leeds agreed a deal to take him to Elland Road on loan with a permanent transfer to follow if they reached the top flight.
Everything was going to plan and the winger even passed his medical and spent deadline day hanging around the Whites’ training ground. But Swansea had second thoughts, pulling out of the deal at the final hour. A few months later he became a Manchester United player, much to Leeds fans' chagrin
Alexis Sanchez to Manchester City, 2017
Everything appeared to be in place for some big Premier League movements on deadline day in August 2017 after Arsenal agreed a British record £92m deal for Monaco’s Thomas Lemar, opening the door for Sanchez’s £60m switch to the Etihad.
However, everything soon collapsed when Lemar decided against joining the Gunners, which in turn saw City miss out on the Chilean as Arsenal decided they could no longer afford to lose him. Judging by how things have gone for Sanchez at Manchester United, maybe it wasn’t such a bad thing after all.
Robinho to Chelsea, 2008
The Brazilian was the first big-name arrival of the Abu Dhabi era at Manchester City, but it took a late bid from the newly-money club to hijack Chelsea’s deal. It was a dramatic turn of events that even confused the player himself.
“I knew I was going to play in England but I didn't know for which team,” Robinho told City TV in 2015. "I was very happy when I found that I had the opportunity to play for Manchester City.”
Zlatan Ibrahimovic to Arsenal, 2000
The Swede met with Arsene Wenger in 2000 to discuss a potential move to London and even posed for pictures holding an Arsenal shirt with his name printed on the back.
However, Wenger made one crucial mistake which ultimately scuppered the deal: he asked Ibrahimovic to have a trial first. "I couldn't believe it,” the striker later said. “I was like, 'No way, Zlatan doesn't do auditions'.”
Emmauel Petit to Tottenham, 1997
An integral part of Arsene Wenger’s first great Arsenal side, Petit has since revealed that he was close to joining the club's north London rivals in 1997. The midfielder held a meeting with then-Spurs chairman Alan Sugar, who tabled a contract offer that Petit said he'd mull over.
Instead, the Frenchman took a taxi - paid for by Sugar, no less - from White Hart Lane to Wenger's house, where he agreed to sign for Arsenal. Ouch.
Paul Gascoigne to Manchester United, 1988
Gascoigne was a man in demand after his exploits at Newcastle, but the midfielder gave Alex Ferguson his word that he would join Manchester United in summer 1988.
Fergie promptly headed off on holiday believing the deal was done, only to be told while sunning himself in Malta that Gazza had signed for Tottenham instead. It would take the Scot another five years to win his first league title at Old Trafford.
Leroy Fer to Aston Villa, 2019
Swansea skipper Fer looked destined for Villa Park at the end of the January transfer window, with the West Midlanders having fought off competition from Lille.
However, Villa had late concerns over the Dutchman’s hamstrings, while Fer had second thoughts about making what he considered to be a sideways step. The move duly fell through and the midfielder instead joined Feyenoord a few months later.
Peter Odemwingie to QPR, 2013
Sky Sports’ deadline-day coverage peaked in 2013 when Odemwingie decided to take things into his own hands to force through a move to QPR. The striker drove all the way to London to try and speed up his proposed transfer, then told the waiting cameras that he was ready to begin a “new chapter”.
It was a shame, then, that the clubs weren’t; a deal couldn’t be struck before the 11pm deadline and Odemwingie was forced to return to the team-mates he'd already said goodbye to. Awkward.
Lee Bowyer to Birmingham, 2005
Bowyer was unsurprisingly put on the market after scrapping with his Newcastle team-mate Kieron Dyer in the middle of a game against Aston Villa, and the Magpies looked to have found a buyer when Birmingham came knocking.
However, a group of Blues fans weren’t happy about the prospect of the midfielder's arrival and began an online protest that made the midfielder change his mind about the move. Fast forward four years and Bowyer ended up at St Andrew's after all.
