| Season | League of Ireland Cup winner | Runner-up | Trophy |
|---|
| 2021 | - | -
League Cup cancelled before play began; no winner. | — |
| 2020 | Abandoned
League Cup abandoned; no winner. |
| 2019 |  Dundalk FC |  Derry City FC
Final: 2-2. Penalties: 6-5. Decided after extra time. | — |
| 2018 | Derry City FC |  Cobh Ramblers FC
Final: 3-1. |  |
| 2017 | Dundalk FC |  Shamrock Rovers FC
Final: 3-0. | |
| 2016 |  St Patrick’s Athletic FC |  Limerick FC
Final: 4-1. | — |
| 2015 | St Patrick’s Athletic FC |  Galway United FC
Final: 0-0. Penalties: 4-3. Decided after extra time. | — |
| 2014 | Dundalk FC | Shamrock Rovers FC
Final: 3-2. | — |
| 2013 | Shamrock Rovers FC |  Drogheda United FC
Final: 2-0. | — |
| 2012 | Drogheda United FC | Shamrock Rovers FC
Final: 3-1. | — |
| 2011 | Derry City FC |  Cork City FC
Final: 1-0. | — |
| 2010 |  Sligo Rovers FC |  Monaghan United
Final: 1-0. | — |
| 2009 |  Bohemian FC |  Waterford United FC
Final: 3-1. | — |
| 2008 | Derry City FC |  Wexford Youths FC
Final: 6-1. | — |
| 2007 | Derry City FC | Bohemian FC
Final: 1-0. Decided after extra time. | — |
| 2006 | Derry City FC |  Shelbourne FC
Final: 0-0. Penalties: 3-0. Decided after extra time. | — |
| 2005 | Derry City FC |  UCD AFC
Final: 2-1. | — |
| 2004 |  Longford Town FC | Bohemian FC
Final: 2-1. | — |
| 2003 | St Patrick’s Athletic FC | Longford Town FC
Final: 1-0. | — |
| 2001/02 | Limerick FC | Derry City FC
Two legs: 2-1, 0-1. Penalties: 3-2. | — |
| 2000/01 | St Patrick’s Athletic FC | UCD AFC
Two legs: 3-1, 2-2. | — |
| 1999/00 | Derry City FC |  Athlone Town AFC
Two legs: 3-1, 2-1. | — |
| 1998/99 | Cork City FC | Shamrock Rovers FC
Two legs: 1-1, 1-0. | — |
| 1997/98 | Sligo Rovers FC | Shelbourne FC
Two legs: 1-0, 0-0. | — |
| 1996/97 | Galway United FC | Cork City FC
Two legs: 3-1, 1-1. | — |
| 1995/96 | Shelbourne FC | Sligo Rovers FC
Aggregate: 2-2. Decided on penalties. | — |
| 1994/95 | Cork City FC | Dundalk FC
Two legs: 1-0, 1-1. | — |
| 1993/94 | Derry City FC | Shelbourne FC
Aggregate: 3-1. | — |
| 1992/93 | Limerick FC | St Patrick’s Athletic FC
Final: 2-0. | — |
| 1991/92 | Derry City FC | Bohemian FC
Final: 1-0. | — |
| 1990/91 | Derry City FC | Limerick City FC
Final: 2-0. | — |
| 1989/90 | Dundalk FC | Derry City FC
Final: 1-1. Penalties: 4-1. | — |
| 1988/89 | Derry City FC | Dundalk FC
Final: 4-0. | — |
| 1987/88 | Cork City FC | Shamrock Rovers FC
Final: 1-0. | — |
| 1986/87 | Dundalk FC | Shamrock Rovers FC
Final: 1-0. | — |
| 1985/86 | Galway United FC | Dundalk FC
Final: 2-0. | — |
| 1984/85 | Waterford United FC |  Finn Harps FC
Final: 2-1. | — |
| 1983/84 | Drogheda United FC | Athlone Town AFC
Final: 3-1. | — |
| 1982/83 | Athlone Town AFC | Dundalk FC
Final: 2-1. | — |
| 1981/82 | Athlone Town AFC | Shamrock Rovers FC
Final: 1-0. | — |
| 1980/81 | Dundalk FC | Galway Rovers FC
Two legs: 0-0, 0-0. Decided on penalties. | — |
| 1979/80 | Athlone Town AFC | St Patrick’s Athletic FC
Final: 4-2. | — |
| 1978/79 | Bohemian FC | Shamrock Rovers FC
Final: 2-0. | — |
| 1977/78 | Dundalk FC | Cork Alberts FC
Two legs: 2-2, 2-2. Decided on penalties. | — |
| 1976/77 | Shamrock Rovers FC | Sligo Rovers FC
Final: 1-0. | — |
| 1975/76 | Limerick FC | Sligo Rovers FC
Two legs: 4-0, 0-1. | — |
| 1974/75 | Bohemian FC | Finn Harps FC
Final: 1-1. | — |
| 1973/74 | Waterford FC | Finn Harps FC
Final: 2-1. | — |
