The 2008–09 season was the 127th season in the history of Tottenham Hotspur Football Club, their 31st consecutive season in the top flight of English football and their 17th consecutive season in the FA Premier League. The club also participated in the FA Cup, Football League Cup and UEFA Cup.
After finishing 11th in the 2007–08 Premier League, Tottenham began the season under the leadership of Spaniard Juande Ramos, drafted in to replace Martin Jol midway through the previous season. However, after suffering the worst start of a league season in Tottenham's history, with no wins in eight league games and only two points, Ramos was sacked and replaced by seasoned manager Harry Redknapp, who quickly eliminated the continental structure that the club had established over the past seasons. 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. 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. With an average attendance of 35,929, Tottenham had the ninth-highest attendance in the Premier League.
Tottenham drafted in a total of 15 players through transfers and sold 19 players during the combined summer and winter transfer windows.
2008–09 season
Pre-season
Transfers
At the end of the 2007–08 season, which saw Tottenham finish 11th in the Premier League, the club announced the signing of Croatian playmaker Luka Modrić and reiterated that any club wishing to sign Bulgarian striker Dimitar Berbatov would need to offer more than £30 million. 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; Černý's loan deal had expired and was not offered a contract extension by Tottenham nor his parent club, Slavia Prague. Little under a month later, Tottenham agreed a deal with Barcelona for 19-year-old Mexican forward Giovani dos Santos for an initial fee of £4.7 million. Not long afterwards, Tottenham reached a deal with Dutch club PSV for Brazilian goalkeeper Heurelho Gomes, valued at around £8 million.
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. Levy said of United boss Alex Ferguson:
"Today's public comments by Manchester United's manager, announcing that he has made an offer for Dimitar and is confident that the deal will go through with time working in their favour, is a blatant example of sheer arrogance and interference with one of our players. 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.
"I have absolutely no wish to sell either player and to date we have not accepted any offer for either. 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. This is the situation we now have on our hands, with both Dimitar and Robbie having made it clear that they wish to leave for Manchester United and Liverpool respectively."
Throughout July, Tottenham parted ways with many first team members of the squad. On 23 July 2008, it was announced that the club had sold the services of Teemu Tainio; the Finnish midfielder joined Sunderland on a three-year contract, while French defender Pascal Chimbonda followed him a day later, joining the same club for an undisclosed fee. 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. Robinson joined the club from Leeds United in May 2004 and made 175 appearances for the club in all competitions, scoring once against Watford in 2007.
On 28 July 2008, Tottenham agreed to sell Robbie Keane to Liverpool for a total that could amount to £20.3 million. With the sale, Tottenham also agreed to drop its official complaint to the Premier League regarding Liverpool's pursuit of Keane after Liverpool issued a formal apology and made a donation to the Tottenham Foundation.
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. I have already made my opinion clear on the nature of this transaction. I don't regard it as a transfer deal – that is something which happens between two clubs when they both agree to trade – this is very much an enforced sale, for which we have agreed a sum of £19m as compensation plus a potential further £1.3m in additional compensation."
On 30 July 2008, French midfielder Steed Malbranque became the third player in a week to leave, following Tainio and Chimbonda to Sunderland for a fee of £7.8 million. Later the same day, Tottenham announced they had reached agreement with Blackburn for the transfer of David Bentley to the club for £15 million.
Totttenham made their first transfer move in the month of August with the signing of veteran goalkeeper César from Real Zaragoza on 8 August 2008. The deal was initially a season-long loan with the permanent signing being completed at the end of the 2008–09 season. The first Tottenham departure in August was French defender Younès Kaboul, who on 11 August 2008 joined Portsmouth for an undisclosed fee. Towards the end of August, two more players left, with Anthony Gardner moving to Hull City and Lee Young-pyo leaving for Borussia Dortmund.
Friendlies As part of their pre-season preparations, Tottenham held a training camp in Spain, along with numerous friendlies, in July. Their first friendly, against local side Tavernes, saw Spurs stroll to an 8–0 success, with Giovanni dos Santos scoring his first goals for the club. Tottenham then faced two of Juande Ramos' former teams in Dénia and Hércules. Spurs beat Dénia 4–2 and then curtailed the Spanish section of their preparations with a 1–1 with Hércules.
Tottenham returned to England to play Norwich City, recovering from being a goal down to win 5–1, with Darren Bent netting four of the strikes. They later played Leyton Orient, again winning 5–1 with Luka Modrić scoring his first goal for Spurs and Bent scoring a hat-trick to take his tally to nine goals in five games. 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. Spurs followed this with another win, over German club Borussia Dortmund 3–0 with goals from Bent, Dos Santos and Jamie O'Hara. Tottenham were crowned the winners of the tournament on 3 August.
Tottenham finished their pre-season preparations with a 5–0 victory over Serie A giants Roma, which ensured they stayed unbeaten throughout the period, scoring 33 goals and conceding 5 in a total of 7 games, with Darren Bent scoring 13 times.
August
Tottenham's league season got off to a poor start with a 2–1 loss to Middlesbrough at the Riverside Stadium, followed a week later by another 2–1 defeat to Sunderland, with debutant Djibril Cissé scoring the winning goal in the final minutes. 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) began to circulate, along with the theory that this refusal from one of Tottenham's best players was hurting team morale. Tottenham got their first point of the season eight days after the Sunderland loss in a 1–1 draw at Stamford Bridge against title contenders Chelsea. With both the end of August and the summer transfer window approaching, the Berbatov saga ended with him making a transfer to Manchester United for £30.75 million and young striker Fraizer Campbell coming on loan for the entire season. Manchester City had tried to enter the fray in the final hours with a £30 million bid accepted but Berbatov rejected the move. Vedran Ćorluka also completed his move from Manchester City to join Croatian teammate Luka Modrić and provide competition for the right-back position.
September Tottenham's first match in September led to another 2–1 loss, at home to Aston Villa. This resulted in three losses in four and one point from a possible twelve, rooting Spurs to the bottom of the Premier League table. Tottenham achieved their first competitive win of the season in the UEFA Cup against Wisła Kraków, with David Bentley scoring his debut and the winning goal. Spurs returned to the league with a goalless home draw against Wigan Athletic and a tepid 2–0 away defeat to Portsmouth, with ex-Tottenham player Jermain Defoe scoring a penalty. At the end of September, Tottenham were bottom of the league and officially suffering their worst Premier League start. 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.
October
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, 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, They then followed this match with another battle against a newly promoted side, Stoke City. The match concluded with Tottenham conceding two penalties and having Michael Dawson and Gareth Bale sent off in a 2–1 loss. This loss meant that Tottenham had only two points from eight games, were bottom of the Premier League and now were amidst the worst start to a season in their 126-year history. 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.
On 25 October, the club announced the departure, with immediate effect, of sporting director Damien Comolli, head coach Juande Ramos and first team coaches Marcos Álvarez and Gus Poyet. 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.
Redknapp was unveiled as Tottenham manager the same day before the home match against Bolton Wanderers and gave the team talk, although the team itself was selected by Clive Allen and Alex Inglethorpe. Tottenham eased to their first league win of the season, with Roman Pavlyuchenko scoring his first Premier League goal.