1988–89 Tottenham Hotspur F.C. season

The 1988–89 season was the 83rd season of competitive football played by Tottenham Hotspur. Entering the 1988–89 season, Terry Venables stayed on as manager for his second season in charge of Tottenham with the team ending in sixth position, nineteen points behind eventual champions Arsenal. In the FA Cup, they got knocked out by second division team, Bradford City and they got knocked out in the fourth round of the Football League Cup by Southampton.

FA Cup
As part of the first division, Tottenham automatically qualified through to the third round of the FA Cup where they was drawn to meet Division Two side Bradford City.

Football League Cup
As part of the first division, Tottenham started the League Cup in the second round where they were drawn to meet third division side, Notts County.