| Charlton Athletic FC v Tottenham Hotspur FC 08/10/1988 | £2.50 | |
| Charlton Athletic FC v Tottenham Hotspur FC 08/10/1988 | £5.00 | |
| Tottenham Hotspur FC v Southampton FC 25/10/1988 | £4.00 | |
| Tottenham Hotspur FC v Blackburn Rovers FC 01/11/1988 | £2.50 | |
| Tottenham Hotspur FC v Coventry City FC 23/11/1988 | £4.50 | |
| Southampton FC v Tottenham Hotspur FC 29/11/1988 | £2.50 | |
| Southampton FC v Tottenham Hotspur FC 29/11/1988 | £3.50 | |
| 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 | |
| Arsenal FC v Tottenham Hotspur FC 02/01/1989 | £2.50 | |
| Bradford City FC v Tottenham Hotspur FC 07/01/1989 | £5.00 |