[4] Not long afterwards, Tottenham reached a deal with Dutch club PSV for Brazilian goalkeeper Heurelho Gomes, valued at around £8 million.

[5] Following comments made by Sir Alex Ferguson indicating confidence over signing Dimitar Berbatov despite negotiations not yet underway, the club issued a press statement on 18 July 2008 on behalf of Daniel Levy, saying that both Manchester United and Liverpool had been reported to the Premier League over comments their respective managers had made which were seen as unsettling both Berbatov and Irish striker Robbie Keane with a view of enticing them away from Tottenham.

It is also probably one of the worst offences by any manager in the Premier League to date and is unbelievably hypocritical given his recent comments in respect of Cristiano Ronaldo and Real Madrid.

[9] The following day, former England goalkeeper Paul Robinson signed a five-year contract with Blackburn Rovers for £3.5 million, having played for Spurs for four years.

[15] Towards the end of August, two more players left, with Anthony Gardner moving to Hull City[16] and Lee Young-pyo leaving for Borussia Dortmund.

[23] Tottenham then embarked to the Netherlands to play in the Feyenoord Jubilee Tournament, held in Rotterdam at the start of August, with a 2–0 victory over Celtic thanks to goals from Bent and David Bentley.

[26] Tottenham's league season got off to a poor start with a 2–1 loss to Middlesbrough at the Riverside Stadium,[27] followed a week later by another 2–1 defeat to Sunderland, with debutant Djibril Cissé scoring the winning goal in the final minutes.

[32] Vedran Ćorluka also completed his move from Manchester City to join Croatian teammate Luka Modrić and provide competition for the right-back position.

[35] Spurs returned to the league with a goalless home draw against Wigan Athletic[36] and a tepid 2–0 away defeat to Portsmouth, with ex-Tottenham player Jermain Defoe scoring a penalty.

Spurs, however, were able to make a successful start to the defence of their League Cup title, defeating Newcastle United 2–1 at St James' Park to progress to the fourth round of the competition.

[38] October started with progression to the group stages of the UEFA Cup for Tottenham with a 1–1 draw in Poland against Wisła Kraków in their second leg tie,[39] but Spurs' horrendous league form continued with a home loss to newly promoted Hull City, Geovanni's long range free-kick in the early minutes of the game condemning Tottenham to another loss,[40] They then followed this match with another battle against a newly promoted side, Stoke City.

The ever-increasing pressure on manager Juande Ramos grew after a 2–0 loss in Italy to Udinese in the first match of the UEFA Cup group stage.

It was announced, within hours, that the club had agreed a deal worth £5 million with Portsmouth to permit manager Harry Redknapp to become the new head coach at Spurs.

Tottenham took the lead with a stunning David Bentley volley from 35-yards, while Arsenal responded with a Mikaël Silvestre header and found themselves 3–1 ahead deep inside the second half.

[46] Dirk Kuyt blasted Liverpool into an early lead before a Jamie Carragher own goal and a Pavlyuchenko tap-in gave Spurs the three points.

[48] Tottenham's fourth game in eleven days sent them to fifth round of the League Cup with a 4–2 win over Liverpool, which also included the first goals for on-loan striker Fraizer Campbell.

Watford had taken the lead through a Tamas Priskin strike but a penalty from Roman Pavlyuchenko and a goal from Darren Bent earned Spurs a tie against Burnley in the semi-finals.

[54] Tottenham continued their decent league form with a 2–0 win over West Ham United which also included Ledley King's first goal in three years.

The 2–0 win was controversial, however, as defender Michael Dawson claimed that he had been fouled by West Brom striker Roman Bednář while the latter scored the opening goal.

[62] Tottenham also signed experienced goalkeeper Carlo Cudicini from Chelsea on a free transfer[63] and also concluded a deal to re-sign Pascal Chimbonda from Sunderland for a fee thought to be around £3 million.

[75] Three days after the extra-time tie, Tottenham faced Manchester United in the FA Cup, losing 2–1, having taken the lead through Pavlyuchenko before a deflected goal from Paul Scholes and a strike from Dimitar Berbatov ended eliminated the side from the competition.

Bolton took a 2–0 lead before a Darren Bent double levelled until another last minute goal from Kevin Davies claimed the points for the home side.

The highly anticipated match ended 0–0 with Spurs enjoying the dominant moments in the game, thanks in part to the first-half sending-off of Arsenal midfielder Emmanuel Eboué.

[84] Tottenham rebounded from the heart-break of the final loss[85] three days later with a comprehensive 4–0 win over Middlesbrough to ease the immediate relegation concerns.

The tense match began with an early goal for Kieran Richardson and remained so until in the dying embers of the game, where Robbie Keane struck a volley to earn Spurs a point.

Tottenham took the lead through a Robbie Keane penalty and led until the 80th minute, when the contentious sending off of Wilson Palacios swung the game back in Blackburn's favour, and two late goals from Benni McCarthy and André Ooijer gave the three points to the home side.

Tottenham led 2–0 through two quick-fire strikes from Darren Bent and Luka Modrić, but in the second-half, United were awarded a penalty by referee Howard Webb and went on to win the game 5–2.

The game was settled by a well-placed Jermaine Jenas effort from just outside the area on the stroke of half-time, and secured Spurs' fifth home win a row.

[100] This was one of many factors that caused Harry Redknapp to go with an unorthodox 3–5–2 formation, notably bringing in Gareth Bale at left wing-back for the Welsh youngster's first league start for four months.

In the second-half, Spurs were forced to rue their earlier missed chances when Valeri Bojinov grabbed an equaliser, in the process scoring the first away goal at the lane since James Beattie's consolation in January.