| Millwall FC v Tottenham Hotspur FC 29/04/1989 | View match | |
| Dagenham FC v Tottenham Hotspur FC 09/05/1989 | View match | |
| Queens Park Rangers FC v Tottenham Hotspur FC 13/05/1989 | £1.50 | |
| Queens Park Rangers FC v Tottenham Hotspur FC 13/05/1989 | £2.50 | |
| Bohemians F.C (Ireland) v Tottenham Hotspur FC 23/07/1989 | View match | |
| Tottenham Hotspur FC v Luton Town FC 19/08/1989 | £4.00 | |
| Tottenham Hotspur FC v Luton Town FC 19/08/1989 | £4.00 | |
| Everton FC v Tottenham Hotspur FC 22/08/1989 | £5.00 | |
| Manchester City FC v Tottenham Hotspur FC 26/08/1989 | £1.75 | |
| Manchester City FC v Tottenham Hotspur FC 26/08/1989 | £4.50 | |
| Aston Villa FC v Tottenham Hotspur FC 09/09/1989 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 16/09/1989 | £3.50 |