Original Puma Tottenham Hotspur 2008/09 football shirt

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.