| Swansea City FC v Tottenham Hotspur FC 06/09/1988 | View match | |
| Tottenham Hotspur FC v Arsenal FC 10/09/1988 | £4.00 | |
| Tottenham Hotspur FC v Arsenal FC 10/09/1988 | View match | |
| Liverpool FC v Tottenham Hotspur FC 17/09/1988 | View match | |
| Tottenham Hotspur FC v Middlesbrough FC 24/09/1988 | £5.00 | |
| Notts County FC v Tottenham Hotspur FC 27/09/1988 | View match | |
| Tottenham Hotspur FC v Manchester United FC 01/10/1988 | £7.50 | |
| 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 Notts County FC 11/10/1988 | £4.00 | |
| Home Farm (Dublin) v Tottenham Hotspur FC 18/10/1988 | View match | |
| Norwich City FC v Tottenham Hotspur FC 22/10/1988 | View match |