| 1968-69 | Omagh Town Swifts | N/A |
| 1969-70 | Maguiresbridge ‘B’ | N/A |
| 1970-71 | Victoria Bridge Reserves | N/A |
| 1971-72 | Maguiresbridge ‘B’ | N/A |
| 1972-73 | Victoria Bridge Reserves | N/A |
| 1973-74 | Dunbreen United | N/A |
| 1974-75 | Victoria Bridge | N/A |
| 1975-76 | Tempo Town | N/A |
| 1976-77 | Dunbreen United | N/A |
| 1977-78 | Dunbreen Rovers Reserves | N/A |
| 1978-79 | Irvinestown Wanderers | N/A |
| 1979-80 | Drumrallagh | N/A |
| 1980-81 | Dergview | N/A |
| 1981-82 | Barrowfield Rovers | N/A |
| 1982-83 | Lisnaskea Rovers | N/A |
| 1983-84 | Blane Rovers | N/A |
| 1984-85 | Victoria Bridge United | N/A |
| 1985-86 | Dunbreen United | N/A |
| 1986-87 | Enniskillen Town United | Fivemiletown United |
| 1987-88 | Barrowfield Killen Rangers | N/A |
| 1988-89 | Tummery Athletic | Ballinamallard United Reserves |
| 1989-90 | Maguiresbridge | Ballinamallard United Reserves |
| 1990-91 | Mountjoy United | Lisnaskea Rovers |
| 1991-92 | Killymore Rovers | Dunbreen Rovers |
| 1992-93 | Omagh Hospitals | Beragh Swifts |
| 1993-94 | Ballinamallard Utd. Reserves | Dunbreen Rovers |
| 1994-95 | Enniskillen Town United Reserves | Lisnarick |
| 1995-96 | Lisnaskea Rovers | Maguiresbridge |
| 1996-97 | Ardstraw | N/A |
| 1997-98 | Killen Rangers | Kevlin United |
| 1998-99 | Sperrin Athletic | N/A |
| 1999-00 | NFC Kesh | N/A |
| 2000-01 | Not Completed | N/A |
| 2001-02 | Sperrin Athletic | Clabby Strollers |
| 2002-03 | Irvinestown Wanderers | N/A |
| 2003-04 | Beragh Swifts | Enniskillen Swifts |
| 2004-05 | Omagh Hospitals | Ardstraw |
| 2005-06 | Lisbellaw United | Kevlin United |
| 2006-07 | Strathroy Harps | Dunbreen Rovers |
| 2007-08 | Churchtown | Shelbourne |
| 2008-09 | Fintona Swifts | Glebe United |
| 2009-10 | Beragh Swifts | Enniskillen Rangers |
| 2010-11 | Strathroy Harps (after play-off) | Dergview Reserves |
| 2011-12 | Strabane Athletic | Killen Rangers |
| 2012-13 | Lisnaskea Rovers | Shelbourne |
| 2013-14 | NFC Kesh | St. Patricks |
| 2014-15 | Enniskillen Santos | Irvinestown Wanderers |
| 2015-16 | Strule United | Magheraveely |
| 2016-17 | Mountjoy United | Lisnaskea Rovers |
2017-18
| Strule United
| Dergview Reserves
|
| 2018-19 | Magheraveely | Omagh Hospitals |
| 2019-20 | Mountfield | Enniskillen Athletic |