| 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 |
| 1932-33 | Omagh Depot | N/A |
| 1933-34 | Omagh Depot | N/A |
| 1934-35 | Enniskillen Corinthians | Enniskillen Celtic |
| 1935-36 | Enniskillen Corinthians | Enniskillen Celtic (play-off) |
| 1936-37 | Omagh Depot | Eniskillen Corinthians |
| 1937-38 | | N/A |
| 1938-39 | R U C Depot | Omagh United |
| 1939-40 | R U C Depot | Enniskillen Corinthians |
| 1940-41 | 8th Foresters | N/A |
| 1941-42 | Enniskillen Corinthians | N/A |
| 1942-43 | R A F | N/A |
| 1943-44 | R A F Killadeas | N/A |
| 1944-45 | R A F Killadeas | N/A |
| 1945-46 | R A F | N/A |
| 1946-47 | N/A | N/A |
| 1947-48 | I T C (Omagh) | Aston Villa (Omagh) |
| 1948-49 | N/A | N/A |
| 1949-50 | N/A | N/A |
| 1950-51 | Fivemiletown United | N/A |
| 1951-52 | Fivemiletown United | Enniskillen Corinthians |
| 1952-53 | Enniskillen Corinthians | Fivemiletown |
| 1953-54 | Enniskillen Corinthians | N/A |
| 1954-55 | Enniskillen Rangers | Enniskillen Corinthians |
| 1955-56 | Enniskillen Corinthians | Enniskillen Rangers |
| 1956-57 | Enniskillen Rangers | Enniskillen Corinthians (play-off) |
| 1957-58 | Ballinamallard | Enniskillen Rangers |
| 1958-59 | Enniskillen Rangers | Enniskillen Corinthians |
| 1959-60 | Brookeborough | Enniskillen Corinthians |
| 1960-61 | Brookeborough | N/A |
| 1961-62 | Enniskillen Rangers | N/A |
| 1962-63 | Enniskillen Rangers | Lisbellaw |
| 1963-64 | Enniskillen Rangers | Enniskillen Corinthians |
| 1964-65 | Enniskillen Rangers | Enniskillen Corinthians |
| 1965-66 | Enniskillen Rangers | Omagh Celtic |
| 1966-67 | Omagh Celtic | Lisnarick |
| 1967-68 | Lisbellaw United | Enniskillen Rangers |
| 1968-69 | Lisbellaw United | Enniskillen Rangers |
| 1969-70 | Enniskillen Corinthians | N/A |
| 1970-71 | Enniskillen Corinthians | Maguiresbridge |
| 1971-72 | Mourneview Celtic | Enniskillen Rangers |
| 1972-73 | Enniskillen Rangers | Irvinestown Wanderers |
| 1973-74 | Kevlin United | Enniskillen Rangers |
| 1974-75 | Kevlin United | Enniskillen Rangers |
| 1975-76 | Lisbellaw United | Dunbreen Rovers |
| 1976-77 | Enniskillen Rangers | Lisnarick |
| 1977-78 | Lisbellaw United | Dunbreen Rovers |
| 1978-79 | Lisbellaw United | Shelbourne |
| 1979-80 | Lisbellaw United | Irvinestown Wanderers |
| 1980-81 | Lisbellaw United | Irvinestown Wanderers |
| 1981-82 | Enniskillen Rangers | Lisbellaw United |
| 1982-83 | Shelbourne | Enniskillen Rangers |
| 1983-84 | Shelbourne | Enniskillen Rangers |
| 1984-85 | Shelbourne | Enniskillen Rangers |
| 1985-86 | Victoria Bridge United | Irvinestown Wanderers |
| 1986-87 | Irvinestown Wanderers | Ballinamallard United |
| 1987-88 | Enniskillen Rangers | Irvinestown Wanderers |
| 1988-89 | Irvinestown Wanders | Enniskillen Rangers |
| 1989-90 | Enniskillen Rangers | Omagh Town Reserves |
| 1990-91 | Enniskillen Rangers | Enniskillen Town United |
| 1991-92 | Enniskillen Rangers (after P/O) | Shelbourne |
| 1992-93 | Shelbourne | Enniskillen Town United |
| 1993-94 | Dergview | Enniskillen Rangers |
| 1994-95 | Shelbourne | Ballinamallard United Reserves |
| 1995-96 | Dergview (after P/O V Enniskillen) | Ballinamallard United Reserves |
| 1996-97 | Dergview | Ballinamallard United Reserves |
| 1997-98 | Ballinamallard United Reserves | Lisnaskea Rovers |
| 1998-99 | Enniskillen Rangers | Killen Rangers |
| 1999-00 | Dergview | Irvinestown Wanderers |
| 2000-01 | Not Completed | N/A |
| 2001-02 | Ballinamallard Utd. Reserves | NFC Kesh/Enniskillen Rangers |
| 2002-03 | Shelbourne (After play-off) | Killen Rangers |
| 2003-04 | Lisnaskea Rovers | Kevlin United |
| 2004-05 | Enniskillen Town United | Irvinestown Wanderers |
| 2005-06 | Enniskillen Town United | Clabby Strollers |
| 2006-07 | Enniskillen Town United | NFC Kesh |
| 2007-08 | Enniskillen Town United | Lisbellaw United |
| 2008-09 | Enniskillen Town United | Lisbellaw United |
| 2009-10 | Lisbellaw United | Glebe United |
| 2010-11 | Lisbellaw United | Enniskillen Town United |
| 2011-12 | Lisbellaw United | Enniskillen Town United |
| 2012-13 | Enniskillen Town United | Lisbellaw United |
| 2013-14 | Strathroy Harps | Enniskillen Town United |
| 2014-15 | Strathroy Harps | Lisbellaw United |
| 2015-16 | Lisbellaw United | Strathroy Harps |
| 2016-17 | Strathroy Harps | Lisbellaw United
|
2017-18
| Enniskillen Rangers
| NFC Kesh
|
| 2018-19 | Enniskillen Rangers | Tummery Athletic |
| 2019-20 | Tummery Athletic | Enniskillen Rangers |