| Brentford FC v Tottenham Hotspur FC 09/05/1986 | View match | |
| West Ham United FC v Tottenham Hotspur FC 12/05/1986 | View match | |
| Tottenham Hotspur FC v Rangers (Glasgow) FC 02/08/1986 | View match | |
| Brighton & Hove Albion FC v Tottenham Hotspur FC 08/08/1986 | View match | |
| Gillingham FC v Tottenham Hotspur FC 12/08/1986 | View match | |
| Barnet FC v Tottenham Hotspur FC 12/08/1986 | View match | |
| Aston Villa FC v Tottenham Hotspur FC 23/08/1986 | View match | |
| Tottenham Hotspur FC v Newcastle United FC 25/08/1986 | £3.50 | |
| Tottenham Hotspur FC v Newcastle United FC 25/08/1986 | £4.50 | |
| Tottenham Hotspur FC v Manchester City FC 30/08/1986 | £4.00 | |
| Tottenham Hotspur FC v Manchester City FC 30/08/1986 | £4.50 | |
| Southampton FC v Tottenham Hotspur FC 02/09/1986 | £2.50 |