| Liverpool FC v Sheffield Wednesday FC 01/02/1969 | View match | |
| Hereford United v Sheffield Wednesday FC 05/02/1969 | View match | |
| Sheffield Wednesday FC v Arsenal FC 01/03/1969 | View match | |
| Sheffield Wednesday FC v West Bromwich Albion FC 05/03/1969 | View match | |
| Coventry City FC v Sheffield Wednesday FC 08/03/1969 | £4.00 | |
| Manchester United FC v Sheffield Wednesday FC 22/03/1969 | £6.00 | |
| Sheffield Wednesday FC v Leeds United FC 01/04/1969 | View match | |
| Sheffield Wednesday FC v West Ham United FC 05/04/1969 | £4.50 | |
| Sheffield Wednesday FC v Nottingham Forest FC 07/04/1969 | View match | |
| Newcastle United FC v Sheffield Wednesday FC 09/04/1969 | £5.00 | |
| Burnley FC v Sheffield Wednesday FC 12/04/1969 | View match | |
| Sheffield Wednesday FC v Leicester City FC 14/04/1969 | View match |