Here are five we believe the club's management will now regret selling
1) Kevin Prince-Boateng
This one is a no-brainer. Prince-Boateng has leapt from Tottenham reserve to AC Milan superstar, although he thrilled Spurs fans with a glorious opener for Milan against Arsenal last month at the San Siro. It wasn't quite an instant rise, Spurs loaned him to Borussia Dortmund and sold him to Portsmouth for £4 million, but they only gave him 24 first team appearances before impatiently casting him aside. The Ghana midfielder is having the last laugh, and is on his way to winning a second successive Serie A title.
2) Darren Bent
Bent will not look back on his Tottenham career fondly, mainly because of the way he was treated by Harry Redknapp, a manager often praised for his man-management skills. Bent was sold to Sunderland and was prolific, scoring 36 goals before being sold to Aston Villa for £24 million. He is one of England's number one strikers, and had he been given a proper chance at Spurs he could have flourished. Unfortunately for him he was at the club with Defoe, Keane and Berbatov, with Redknapp making clear he was always fourth choice, usually starting him off the substitutes bench, nevertheless he scored 25 goals, and his goals per minutes ratio was far better than his goals per game ratio would suggest.
3) Peter Crouch Can anyone seriously argue that Louis Saha is an improvement on Peter Crouch? The lanky giant may not be everybody's cup of tea, but he scored goals, important goals. Including the winner away to AC Milan and one away to Manchester City which helped them qualify for the Champions League- and no we're not talking about last season's own goal. He gave the club a different option, linked well with Rafael van der Vaart and would surely much rather still be at Tottenham than Stoke City. With Spurs due to qualify for the Champions Legue next season, he would again have been a useful weapon.
4) Paul Robinson Yes goalkeeper Paul Robinson was going through a rough patch, but were any of his mistakes as big clangers as ones his replacement Heurelho Gomes made?
Robinson has been consistent at Blackburn, and while Spurs have Brad Friedel now, he only has one more season left in him, whereas Robinson can play on for several years yet. Spurs should never have let him go. He was a victim principally of Tottenham's many changes in managers, with new bosses prompting changes. He was also going through a rough phase at the time, with a couple of high-profile mistakes for England weighing on his shoulders, but his club should have stuck by him and not been so quick to sell him.
5) Danny Murphy
Danny Murphy was sold after just one season at White Hart Lane, too soon for any player to bed in and improve at any club. Years later Murphy was orchestrating Fulham's run to the Europa League Final. Would those talents have been welcome at Tottenham, you bet. We're not saying he should be in the Spurs team right now, but over the past four seasons he would have been a very valuable member of the first team.
image: © Mafue