
| Overall | Div 1 | |
| Wins | 692 | 144 |
| Draws | 380 | 36 |
| Losses | 765 | 120 |
| Pct. | 0.480 | 0.540 |
| (S3-5), Terry Bray (S6-9), Len Lear (S10-11), Nick Vatmanidis (S12-12), David Blair (S39-41), |
| M | DATE | SCORE | OPPONENT | COMPETITION | HEAD TO HEAD RESULTS | LAST MATCH | |||
| 1 | Sep 27 | L | 2 - 5 | @ | Forfar Athletic | CECIL Cup | Cowdenbeath lead series 20-6-19 | ||
| 2 | Oct 01 | W | 3 - 1 | Forfar Athletic | CECIL Cup | Cowdenbeath lead series 20-6-19 | |||
| 3 | Oct 04 | W | 5 - 0 | Dundee United | Division 2 | Dundee United lead series 17-7-10 | |||
| 4 | Oct 04 | W | 1 - 0 | @ | Annan Athletic | Division 2 | Cowdenbeath lead series 13-9-11 | ||
| 6 | Oct 11 | L | 0 - 5 | @ | Alloa Athletic | Division 2 | Cowdenbeath lead series 28-12-19 | ||
| 7 | Oct 11 | L | 3 - 4 | Elgin City | Division 2 | Cowdenbeath lead series 24-14-16 | |||
| 9 | Oct 18 | L | 1 - 2 | @ | Nairn County | Division 2 | Nairn County lead series 26-10-20 | ||
| 10 | Oct 18 | W | 1 - 0 | Saint Mirren | Division 2 | Saint Mirren lead series 21-5-14 | |||
| 12 | Oct 25 | L | 0 - 4 | @ | Kilmarnock | Division 2 | Kilmarnock lead series 13-4-11 | ||
| 13 | Oct 25 | W | 5 - 1 | East Fife | Division 2 | East Fife lead series 14-6-13 | |||
| 15 | Nov 01 | D | 2 - 2 | @ | Cove Rangers | Division 2 | Cove Rangers lead series 4-1-3 | ||
| 16 | Nov 01 | W | 3 - 1 | Clyde FC | Division 2 | Cowdenbeath lead series 32-8-20 | |||
| 19 | Nov 08 | D | 4 - 4 | Edinburgh City | Division 2 | Edinburgh City lead series 5-7-1 | |||
| 20 | Nov 08 | L | 1 - 6 | @ | Hibernian | Division 2 | Hibernian lead series 19-9-7 | ||
| 23 | Nov 15 | W | 5 - 1 | Queen of the South | Division 2 | Series even at 13-4-13 | |||
| 24 | Nov 15 | L | 2 - 3 | @ | Partick Thistle | Division 2 | Cowdenbeath lead series 21-10-14 | ||
| 26 | Nov 22 | W | 4 - 1 | Forfar Athletic | Division 2 | Cowdenbeath lead series 20-6-19 | |||
| 27 | Nov 22 | L | 3 - 5 | @ | Dundee United | Division 2 | Dundee United lead series 17-7-10 | ||
| 28 | Nov 26 | L | 0 - 3 | (n) | Dundee FC | SESL CUP | Series even at 23-12-23 | ||
| 29 | Nov 29 | (n) | Airdrieonians FC | SESL CUP | Cowdenbeath lead series 15-6-7 | COW 7-3 (Sea-56) | |||
| 30 | Nov 29 | (n) | Nairn County | SESL CUP | Nairn County lead series 26-10-20 | NAI 2-1 (Sea-60) | |||
| 31 | Dec 01 | (n) | Brechin City | SESL CUP | Cowdenbeath lead series 17-11-11 | Draw 1-1 (Sea-55) | |||
| 32 | Dec 03 | (n) | Dundee United | SESL CUP | Dundee United lead series 17-7-10 | DUU 5-3 (Sea-60) | |||
| 33 | Dec 06 | Annan Athletic | Division 2 | Cowdenbeath lead series 13-9-11 | COW 1-0 (Sea-60) | ||||
| 34 | Dec 06 | Alloa Athletic | Division 2 | Cowdenbeath lead series 28-12-19 | ALO 5-0 (Sea-60) | ||||
| 35 | Dec 13 | @ | Elgin City | Division 2 | Cowdenbeath lead series 24-14-16 | ELG 4-3 (Sea-60) | |||
| 36 | Dec 13 | Nairn County | Division 2 | Nairn County lead series 26-10-20 | NAI 2-1 (Sea-60) | ||||