| SEASON | WINNERS | RUNNERS-UP |
| 1904-05 | St. Michael’s Hall Celtic | Enniskillen Corinthians |
| 1905-06 | St. Michael’s Hall Celtic | N/A |
| 1906-07 | Sligo Athletic | N/A |
| 1907-08 | St. Michael’s Hall Celtic | N/A |
| 1908-09 | St. Michael’s Hall Celtic | N/A |
| 1909-10 | St. Michael’s Hall Celtic | N/A |
| 1910-11 | Clones Celtic | N/A |
| 1911-12 | R Irish Fusiliers (Cavan) | N/A |
| 1912-13 | Irvinestown Wanderers | N/A |
| 1913-14 | N/A | N/A |
| 1914-15 | N/A | N/A |
| 1915-16 | N/A | N/A |
| 1916-17 | N/A | N/A |
| 1917-18 | N/A | N/A |
| 1918-19 | N/A | N/A |
| 1919-20 | Omagh Wanderers | Enniskillen Corinthians |
| 1920-21 | Enniskillen Corinthians | N/A |
| 1921-22 | Omagh Wanderers | N/A |
| 1922-23 | Enniskillen Corinthians | N/A |
| 1923-24 | Fermanagh Constabulary | N/A |
| 1924-25 | Melvin United | N/A |
| 1925-26 | Ballinamallard | N/A |
| 1926-27 | Enniskillen Corinthians | N/A |
| 1927-28 | Enniskillen Corinthians | N/A |
| 1928-29 | Enniskillen Corinthians | Enniskillen Celtic (play-off) |
| 1929-30 | R Inniskilling + R Irish Fusiliers | Enniskillen G.N.R. |
| 1930-31 | Enniskillen GNR | N/A |
| 1931-32 | Omagh United Omagh Depot | N/A |