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. Spurs beat Dénia 4–2[20] and then curtailed the Spanish section of their preparations with a 1–1 with Hércules.

or debate this issue live on our message boards. [69], January began well for Tottenham, advancing to the next round of the FA Cup with a 3–1 win over Wigan[70] and then following that with a 4–1 win against Burnley in the League Cup semi-final first leg.

[89], Tottenham faced Chelsea in the final match in March at White Hart Lane. 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. [12] Both Joel Obi and Nwankwo Obiora signed co-ownership by Parma, however Obi will remain with Inter and Nwankwo will spend the rest of the season with Parma. View comments. Eight of the 25 need to be 'homegrown', which means they must have been trained in England or Wales for three seasons before they turned 21. Webb later admitted that he had got the penalty decision wrong. [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. The match was heading for a 1–1 draw until Damien Duff scored in stoppage time to give Newcastle the three points. Throughout July, Tottenham parted ways with many first team members of the squad. [96], April ended with a defeat to league leaders Manchester United at Old Trafford. Having made their worst start to a league season in their 126-year history, Tottenham made a three place improvement on the 2007–08 season. [28] The defeats against Middlesbrough and Sunderland were punctuated with the ongoing transfer saga concerning Dimitar Berbatov and Manchester United; rumours that Berbatov had refused to play (later revealed to be true[29]) began to circulate, along with the theory that this refusal from one of Tottenham's best players was hurting team morale. [2] Tottenham's transfer movement began immediately, with Czech goalkeeper Radek Černý moving on a free transfer to Queens Park Rangers following the end of the season;[3] Černý's loan deal had expired and was not offered a contract extension by Tottenham nor his parent club, Slavia Prague.

However, when a player's head is turned and their commitment is absent, particularly when they occupy key positions such as that of striker, they become a negative influence in a team dressing room in which they were once a positive addition and influence. [17], As part of their pre-season preparations, Tottenham held a training camp in Spain, along with numerous friendlies, in July. Spurs finished the season in eighth, a turnaround in form pushing them into higher reaches of the league, when they were as low as 19th place as recently as January and 20th for a part of the season. [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.

[65], The departures in January saw Andy Barcham made his loan move to Gillingham permanently for an undisclosed fee. [10] On the last day of winter transfer window, Inter sent Nelson Rivas to Dnipro Dnipropetrovsk on loan,[11] and brought Yuto Nagatomo from Cesena as part of the deal that sent Davide Santon in the opposite direction, also on loan. 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. On 6 January 2009, Jermain Defoe returned to the club from Portsmouth in a deal worth an initial £9 million, with extras and the writing-off of past transfer fees in Pedro Mendes and Defoe himself; the media announced the total fee at £15 million. In a thrilling London derby, Tottenham took maximum points thanks to a second-half goal from Luka Modrić and a much improved performance by goalkeeper Heurelho Gomes, putting Tottenham only three away from a European place. Tottenham Hotspur 2008–09 football season, "Luka Modric happy to sleep with Spurs' enemy", "Giovani transferred to Tottenham Hotspur", "BBC Sport – Football – Defender Younes Kaboul rejoins Tottenham", "Norske Dag Alexander (19) klar for Valencia", "Prince-Boateng loan to Borussia Dortmund", https://en.wikipedia.org/w/index.php?title=2008–09_Tottenham_Hotspur_F.C._season&oldid=979874021, Short description is different from Wikidata, Articles with unsourced statements from September 2020, Creative Commons Attribution-ShareAlike License, This page was last edited on 23 September 2020, at 08:14. Tottenham took on relegation strugglers West Brom at White Hart Lane, looking to bounce back from the heavy defeat at Old Trafford.

[101], The following Saturday, Tottenham went into their final home game of the season against Manchester City, with a target of setting a new club record for goals conceded at home. [98], Against the norm, there were four Premier League fixtures in May. [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.

Spurs also reached the final of the League Cup, and, as the reigning champions, faced league leaders Manchester United but lost 4–1 on penalties.

[37] At the end of September, Tottenham were bottom of the league and officially suffering their worst Premier League start. After this win, however, on 23 December, due to his poor performance in Serie A and separated by 13 points from the leader Milan, Inter announced on its website the departure of Rafael Benítez[4] to be replaced by Leonardo the following day.[5]. Tottenham were crowned the winners of the tournament on 3 August. Tottenham's league form improved and mainly remained positive with the final position of eighth a far cry from the relegation places Tottenham had occupied throughout the campaign. Note: Flags indicate national team as defined under FIFA eligibility rules.

Players may hold more than one non-FIFA nationality. 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. 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. Meanwhile, the winter transfer window for Inter was busy with transfers. [14] The first Tottenham departure in August was French defender Younès Kaboul, who on 11 August 2008 joined Portsmouth for an undisclosed fee. Inter won their match against Napoli with two goals from Thiago Motta and another one form Esteban Cambiasso. Tottenham eased to their first league win of the season, with Roman Pavlyuchenko scoring his first Premier League goal. [53], Tottenham began December by putting themselves into the semi-finals of the League Cup with a 2–1 win over Watford. [7] On 28 January, Inter announced the signing of Giampaolo Pazzini from Sampdoria, as part of the deal that saw Jonathan Biabiany join Sampdoria. [68] Two days later, Tottenham outcast Hossam Ghaly joined Saudi Arabian club Al Nassr for an undisclosed fee. Brilliant play saw Spurs take a 3–0 lead in the first 30 minutes before James Beattie scored a consolation goal for the visitors. [3] Inter completed The Quintuple, becoming the fourth team in the world after Liverpool in 2001, Al-Ahly in 2006 and Barcelona in 2009. Levy issued a statement coinciding with the confirmation of the Keane transfer: "I was incredibly disappointed when I first heard, not only that Liverpool had been working behind the scenes to bring Robbie to Anfield, but that Robbie himself wanted to go and he submitted a transfer request to this effect.