| Bashley v Tottenham Hotspur FC 13/12/1988 | View match | |
| West Ham United FC v Tottenham Hotspur FC 17/12/1988 | £4.50 | |
| Tottenham Hotspur FC v Luton Town FC 26/12/1988 | £3.00 | |
| Tottenham Hotspur FC v Luton Town FC 26/12/1988 | £2.00 | |
| Tottenham Hotspur FC v Newcastle United FC 31/12/1988 | View match | |
| Arsenal FC v Tottenham Hotspur FC 02/01/1989 | £2.50 | |
| Arsenal FC v Tottenham Hotspur FC 02/01/1989 | £5.00 | |
| Bradford City FC v Tottenham Hotspur FC 07/01/1989 | £5.00 | |
| Leytonstone & Ilford v Tottenham Hotspur FC 12/01/1989 | View match | |
| Tottenham Hotspur FC v Nottingham Forest FC 15/01/1989 | View match | |
| Tottenham Hotspur FC v AS Monaco 17/01/1989 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 21/01/1989 | View match |