The campaign featured Tottenham's first ever involvement in the UEFA Champions League, with the club entering via the play-off round after finishing fourth in the 2009–10 season.

Early in the transfer window, Tottenham retained the services of a number of key players, with club captain Ledley King signing a new two-year contract extension with the club,[38] closely followed by former Chelsea goalkeeper Carlo Cudicini, who signed a new one-year contract following his recovery from a serious road accident sustained in November 2009.

As a result of the move, Gallas became the first Premier League player to play for Chelsea, Arsenal and Tottenham Hotspur, all London clubs and fierce rivals.

[11] This looked to be Spurs' only move of the day, but in the final few moments before the deadline, news broke that Tottenham were in negotiations with Real Madrid midfielder Rafael van der Vaart.

Following the closure of the transfer window, the club had to wait for the deal to be ratified by the Premier League, due to complications on Spurs' computer.

Soon after, a number of fringe and academy players, including veteran goalkeeper Jimmy Walker, left the club on free transfers.

[19] Six days later, winger Andros Townsend signed a season-long loan for Ipswich Town after featuring for Tottenham in their pre-season tour of the United States.

[15] The following day, Ryan Mason, who also featured in Spurs' pre-season, joined Doncaster Rovers on a one-month deal,[42] trailed a week later with young striker Jon Obika clinching a move to Crystal Palace for the season.

A fairly quiet window ended with senior players Robbie Keane, Giovani dos Santos and Jamie O'Hara joining West Ham United, Racing de Santander and Wolverhampton Wanderers on loan deals, respectively.

Henry opened the scoring against his old rivals, before goals from Robbie Keane and Gareth Bale in the second half gave Spurs the 2–1 win.

Midway through the first half, Villarreal took the lead with former Manchester United striker Giuseppe Rossi finishing a Santi Cazorla through-ball.

Spurs ended up lifting the trophy after securing a 1–0 win, with Gareth Bale scoring the only goal of the game early into the second half.