| 1974/75 | Port Orient Battery | Carmichael Town |
| 1975/76 | Racing Club | Edwalton, Eleanor's Bay Cosmos, Worthington Rovers |
| 1976/77 | Gresdon Methodists | Deportivo León, Little Padstow, AFC Droy |
| 1977/78 | St Vincent All Stars | Sancti Spiritus, New Lincoln University |
| 1978/79 | Adelaide Wanderers | Edwalton, Worthington Rovers |
| 1979/80 | Jessopstown Rangers | Clifton Albion, Kingsport Bohemians |
| 1980/81 | Courteney Villa | AFC Droy, St Vincent All Stars, Port Orient Battery |
| 1981/82 | Edwalton | West Walpool Juniors, Kingsport Bohemians |
| 1982/83 | Worthington Rovers | Gresdon Methodists, Hoxbeth Amateurs |
| 1983/84 | Port Fowey Royals | Wincanton Athletic, Courteney Villa, Baptist Railway Athletic |
| 1984/85 | Adelaide Wanderers | Little Antonito, Whitburn Carew |
| 1985/86 | Port Fowey Royals | Santiago de Brados, Little Padstow |
| 1986/87 | Hereford & Aspley | Eleanor's Bay Cosmos, Baptist Railway Athletic |
| 1987/88 | South Bay Sports | Deportivo León, Little Padstow |
| 1988/89 | Durham West End | Worthington Rovers, Palmerston United |
| 1989/90 | Jessopstown Rangers | Sancti Spiritus, Edwalton |
| 1990/91 | Deportivo León | Wincanton Athletic, Kingsport Bohemians |
| 1991/92 | Jessopstown Rangers | Santiago de Brados, Clifton Albion, Eleanor's Bay Cosmos |
| 1992/93 | St Vincent All Stars | Courteney Villa, Racing Club |
| 1993/94 | Little Antonito | West Walpool Juniors, Wincanton Athletic |
| 1994/95 | Worthington Rovers | Santiago de Brados, Little Padstow |
| 1995/96 | AFC Droy | South Bay Sports, Sancti Spiritus |
| 1996/97 | Kingsport Bohemians | Hereford & Aspley, Edwalton, Deportivo León |
| 1997/98 | Sancti Spiritus | Carmichael Town, Gresdon Methodists |
| 1998/99 | Hereford & Aspley | Port Orient Battery, Courteney Villa |
| 1999/00 | Lansdowne 1981 | Santiago de Brados, Holloway Sands |
| 2000/01 | Jessopstown Rangers | Durham West End, Serjeant's Bay, Hoxbeth Amateurs |
| 2001/02 | St Vincent All Stars | Courteney Villa, Wincanton Athletic |
| 2002/03 | Port Fowey Royals | Baptist Railway Athletic, West Walpool Juniors |
| 2003/04 | Palmerston United | Holloway Sands, Eleanor's Bay Cosmos |
| 2004/05 | Little Padstow | West Walpool Juniors, Baptist Railway Athletic |
| 2005/06 | Whitburn Carew | Lansdowne 1981, South Bay Sports |
| 2006/07 | Hoxbeth Amateurs | Kintyre Coastguard, Wyvernmouth Dockers |
| 2007/08 | Deportivo León | Little Padstow, Gresdon Methodists |
| 2008/09 | Jessopstown Rangers | Adelaide Wanderers, St Vincent All Stars, Santiago de Brados |
| 2009/10 | Durham West End | Palmerston United, Racing Club |
| 2010/11 | South Bay Sports | Kingsport Bohemians, Real San Domingo |
| 2011/12 | Santiago de Brados | Adelaide Wanderers, St Vincent All Stars |
| 2012/13 | Port Fowey Royals | Holloway Sands, Racing Club |
| 2013/14 | West Walpool Juniors | Palmerston United, Sancti Spiritus |
| 2014/15 | Clifton Albion | Durham West End, Serjeant's Bay |
| 2015/16 | Jessopstown Rangers | Sancti Spiritus, Adelaide Wanderers |
| 2016/17 | AFC Droy | Lansdowne 1981, Racing Club |
| 2017/18 | Worthington Rovers | Carlton Town, Sancti Spiritus |
| 2018/19 | Durham West End | Palmerston United, Clifton Albion |
| 2019/20 | St Vincent All Stars | Real San Domingo, Deportivo León |
| 2020/21 | Baptist Railway Athletic | Carmichael Town, Wincanton Athletic, Little Padstow |
| 2021/22 | Edwalton | Gresdon Methodists, Carlton Town |
| 2022/23 | Hereford & Aspley | Real San Domingo, New Lincoln University |
| 2023/24 | West Walpool Juniors | Hoxbeth Amateurs, Little Padstow, Eleanor's Bay Cosmos |
| 2024/25 | St Vincent All Stars | Santiago de Brados, Clifton Albion |
| 2025/26 | Worthington Rovers | Eleanor's Bay Cosmos, Sancti Spiritus |