Goalkeeper Robert Green made several saves before ex-West Ham player Jermain Defoe returned to haunt his former club with a finish from close range to send Spurs to the final.

Robbie Keane claimed two goals, one from open play and one from the penalty spot, and Aaron Lennon wrapped up the game with a tap-in, supplied by new signing Kyle Naughton.

Vedran Ćorluka's first goal for Spurs put daylight between the two teams and then a solo run from Jermain Defoe made the game safe at 3–0 and ended their only home fixture of the pre-season with a win.

Spurs eased their way to a 5–1 victory over their lower league opponents, with the additional bonus of five different goal scorers: strikes from Tom Huddlestone, Jamie O'Hara, Peter Crouch, David Bentley and Roman Pavlyuchenko sealed the win and passage to the next round.

The game was marred for Spurs, however, as it was confirmed that influential midfielder Luka Modrić had suffered a fracture to his fibula, forcing him to miss many weeks in the season.

[29][30] Following Tottenham's 2–1 win over Birmingham in which Modrić had suffered a broken leg, Spurs entered transfer window deadline day in pursuit of a midfielder.

[39] Jon Obika joined his fellow Spurs loanees at Yeovil in mid-August, putting pen to paper for an initial one-month loan.

[41] The last loans of the summer transfer window involved three youth goalkeepers, with David Button, Oscar Jansson and Lee Butcher joining Crewe Alexandra, Exeter City and Grays Athletic respectively.

[46] After the first loss of the season, Tottenham then had the challenge of Chelsea at Stamford Bridge, and although Spurs stayed in the game for long periods, they eventually succumbed to a 3–0 defeat.

Portsmouth had started the season very poorly and experiencing off-field trouble involving various owners of the club, Tottenham took the lead early in the game on the 29th-minute mark with Ledley King powering in a header from a Niko Kranjčar Corner, Spurs doubled their lead on half time with Jermain Defoe sliding the ball home from a Jermaine Jenas through-ball.

Portsmouth began to battle in the second half and scored a goal through ex-Tottenham player Kevin-Prince Boateng and following Jermain Defoe's red card for a stamp on Aaron Mokoena, a tense finish ensued, however after the injury time sending off of Michael Brown, Tottenham secured the three points.

[53] Tottenham ended October with a North London derby against Arsenal at the Emirates Stadium, Spurs entered the game without Luka Modrić, Aaron Lennon and the suspended Jermain Defoe and the absences meant that David Bentley made his first start of the season against his former club.

Steed Malbranque, Andy Reid, Márton Fülöp, Fraizer Campbell and Darren Bent, making his first return to the Lane since his acrimonious departure in the summer.

Spurs fought back and in the 78th minute grabbed an equaliser with Michael Dawson hitting a volley into the net from just outside the area, earning a point for Tottenham and lifting the team into third place.

[65] Two days later saw the return of another former player Younès Kaboul, re-signed from Portsmouth for a fee believed to be around £5 million in what was Tottenham's only permanent signing of the window.

[67] The only other outright leaving in January belonged to Troy Archibald-Henville, who after two successful loan spells with Exeter moved to Saint James' Park permanently, again for an undisclosed fee.

[75] Tottenham began the month with FA Cup duty, on 2 January, with a third-round tie against Peterborough United at White Hart Lane.

[81] The FA Cup opened February for Tottenham, facing Leeds United in a fourth-round replay following the 2–2 draw at White Hart Lane in late January.

[82] Three days later, on 6 February, Spurs competed in their first Premier League match of the month, facing fellow top four contenders, Aston Villa at home.

Spurs controlled the first half and took the lead early through Roman Pavlyuchenko, with his fifth goal in three games, and a stunning Luka Modrić effort following good build-up play through Croatian compatriots Niko Kranjčar and Vedran Ćorluka.

[88] March began with Tottenham's trip to Craven Cottage to face Fulham in the FA Cup, where the tie ended 0–0, resulting in a replay having to be played later in the month.

Tottenham extended their lead early in the second half through Roman Pavlyuchenko before Christopher Samba gave Blackburn hope, bringing the score line back to 2–1.

Spurs rung the changes at half-time, making two substitutions and one immediately paid off, as the newly introduced David Bentley scored a free-kick to equalise the game.

Tottenham took the lead ten minutes later through a Roman Pavlyuchenko volley and then put their name in the semi-final draw when Eiður Guðjohnsen squeezed home the third Spurs goal of the game.

Darren Bent scored against his former club within a minute, stabbing home from close range from an early corner to give Sunderland the lead.

Peter Crouch had a goal wrongly ruled out in the second half of extra time before ex-Tottenham player Kevin-Prince Boateng sealed the final place for Portsmouth with a last-minute penalty.

The introduction of the returning Robin van Persie led Gomes to make three miraculous saves to ensure Tottenham's lead before Nicklas Bendtner gave Arsenal a late consolation marker.

Terry saw red in the second half for two bookable offences of Pavlyuchenko and Bale respectively before Frank Lampard got a late consolation in injury time, but Spurs held on for another invaluable three points.

The game looked to be heading for a draw until in the 82nd minute, Peter Crouch scored a close-range header to give Tottenham the win and ensure the club Champions League football for the first time.

Tottenham took an early lead with Gareth Bale powering home in the third minute, then doubled the advantage after a Luka Modrić solo effort.