| 15 Aug ’04 | Caludon | 2-0 | Old Shepherd | – | Sowe Common | Friendly |
| Aug 22 ’04 | Shepherd AFC | 8-6 | Old Shepherd | Burke (4), Davis (2) | Coundon Park | Friendly |
| Sep 12 ’04 | Coventry Rangers Res. | 2-2 | Old Shepherd | Davis, Burke | Memorial Park | League |
| Sep 19 ’04 | Old Shepherd | 3-4 | Cryfield Grange | K. Gilmore, Chester, Barnett (aet, 3-3 full time) | President Kennedy School | Tom Cooke Cup – 1st Round |
| Sep 26 ’04 | Centaur (Prem) | 4-3 | Old Shepherd | Davis, Ariss, Phillips | Bishop Ullathorne | Gary James Cup – 2nd Round |
| Oct 3 ’04 | Old Shepherd | 2-4 | Coventry Eagle | Davis (2) | President Kennedy School | League |
| Oct 10 ’04 | Premier Athletic | 2-3 | Old Shepherd | Barnett, Davis, Burke | Foxford School | League |
| Oct 17 ’04 | Old Shepherd | 4-4 | Swanswell Reserves | Davis, Ayres, K. Gilmore (2) | President Kennedy School | League |
| Nov 7 ’04 | Coundon Hotel | 4-0 | Old Shepherd | – | Coundon Park | League |
| Nov 28 ’04 | Old Shepherd | 6-0 | Premier Athletic | Davis (4), K. Gilmore (2) | President Kennedy School | League |
| Dec 12 ’04 | Old Shepherd | 3-4 | Arches | Davis (2), Burke | President Kennedy School | League |
| Dec 19 ’04 | Our Lady (Prem) | 2-0 | Old Shepherd | – | Floyds Field | Maurice James Cup |
| Jan 2 ’05 | Lindfield (Prem) | 2-4 | Old Shepherd | OG, Davis (2), Burke (pen) | Coundon Park | Maurice James Cup |
| Jan 9 ’05 | Old Shepherd | 2-9 | Coundon Hotel | OG, Burke | President Kennedy School | League |
| Jan 16 ’05 | Coventry Eagle | 6-2 | Old Shepherd | Davis (2) | Coundon Park | Maurice James Cup |
| Jan 23 ’05 | Old Shepherd | 0-1 | Hastings Tavern | – | President Kennedy School | Maurice James Cup |
| Jan 30 ’05 | Stoke Heath Rangers | 5-4 | Old Shepherd | Davis (2), Chester, Burke | Coundon Park | League |
| Feb 20 ’05 | Cryfield Grange | 2-6 | Old Shepherd | Deslandes (2), K. Gilmore (3), Flanagan | Coundon Park | League |
| Mar 6 ’05 | Old Shepherd | 1-4 | Hastings Tavern | Deslandes | Foleshill Park | League |
| Mar 13 ’05 | Hastings Tavern | 4-1 | Old Shepherd | OG | Stonebridge Esate | League |
| Apr 3 ’05 | Arches | 0-4 | Old Shepherd | Davies, K. Gilmore (2), A. Gilmore | Coundon park | League |
| Apr 10 ’05 | Old Shepherd | 0-0 | Cryfield Grange | – | Coundon Park | League |
| Apr 17 ’05 | Charterhouse (Eagle) | 5-4 | Old Shepherd | Barber, Deslandes, Davis, Chester | Coundon Park | League |
| Apr 24 ’05 | Old Shepherd | 2-0 | Coventry Rangers Res. | Barber, Barnett | President Kennedy School | League |
| May 22 ’05 | Old Shepherd | 3-3 | Stoke Heath Rangers | K. Gilmore (2), Deslandes | President Kennedy School | League |
