| Tottenham Hotspur FC v Millwall FC 10/12/1988 | £4.00 | |
| 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 | |
| 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 | |
| Manchester United FC v Tottenham Hotspur FC 05/02/1989 | £2.00 | |
| Manchester United FC v Tottenham Hotspur FC 05/02/1989 | £3.00 | |
| Tottenham Hotspur FC v Charlton Athletic FC 11/02/1989 | £4.00 | |
| Tottenham Hotspur FC v Norwich City FC 21/02/1989 | £2.50 | |
| Tottenham Hotspur FC v Norwich City FC 21/02/1989 | £3.00 |