The 2008–09 season was Tottenham Hotspur's 17th season in the Premier League, their 30th successive season in the top division of the English football league system and the 126th year of their history.

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.

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.

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