| 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 | |
| Portsmouth FC v Tottenham Hotspur FC 28/01/1989 | View match | |
| Manchester United FC v Tottenham Hotspur FC 05/02/1989 | £3.00 | |
| Manchester United FC v Tottenham Hotspur FC 05/02/1989 | £2.00 | |
| Tottenham Hotspur FC v Charlton Athletic FC 11/02/1989 | £4.00 |