| Chelsea FC v Wolverhampton Wanderers FC 14/12/1968 | £4.50 | |
| Wolverhampton Wanderers FC v Sheffield Wednesday FC 21/12/1968 | View match | |
| Hull City FC v Wolverhampton Wanderers FC 04/01/1969 | £6.00 | |
| Wolverhampton Wanderers FC v Nottingham Forest FC 11/01/1969 | View match | |
| West Ham United FC v Wolverhampton Wanderers FC 18/01/1969 | View match | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £2.50 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £2.00 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £2.50 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £4.50 | |
| Tottenham Hotspur FC v Wolverhampton Wanderers FC 25/01/1969 | £3.00 | |
| Everton FC v Wolverhampton Wanderers FC 28/01/1969 | View match | |
| Wolverhampton Wanderers FC v Burnley FC 01/02/1969 | View match |