Irregularly held super cup between league champion and cup winner; the first two titles were shared.
| Season | Northern Irish Charity Shield winner | Runner-up | Trophy |
|---|---|---|---|
| 2025/26 | Larne FC | Coleraine FC Final: 0-0. Decided on penalties. Played on July 3, 2026. |  |
| 2024/25 | Dungannon Swifts FC | Linfield FC Final: 0-0. Penalties: 3-5. | |
| 2023/24 | Larne FC | Cliftonville FC Final: 2-1. | |
| 2022/23 | Crusaders FC | Larne FC Final: 0-2. | — |
| 2021/22 | Crusaders FC | Linfield FC Final: 0-2. | — |
| 2020/21 | - | - The Charity Shield was not held. | — |
| 2019/20 | - | - The Charity Shield was not held. | — |
| 2018/19 | - | - The Charity Shield was not held. | — |
| 2017/18 | - | - The Charity Shield was not held. | — |
| 2016/17 | Linfield FC | Coleraine FC Final: 3-1. | — |
| 2015/16 | Glenavon FC | Crusaders FC Final: 0-1. | — |
| 2014/15 | Glentoran FC | Crusaders FC Final: 0-1. | — |
| 2013/14 | Cliftonville FC | Ballymena United FC Final: 0-0. Penalties: 4-2. | — |
| 2012/13 | - | - The Charity Shield was not held. | — |
| 2011/12 | - | - The Charity Shield was not held. | — |
| 2010/11 | - | - The Charity Shield was not held. | — |
| 2009/10 | - | - The Charity Shield was not held. | — |
| 2008/09 | - | - The Charity Shield was not held. | — |
| 2007/08 | - | - The Charity Shield was not held. | — |
| 2006/07 | - | - The Charity Shield was not held. | — |
| 2005/06 | - | - The Charity Shield was not held. | — |
| 2004/05 | - | - The Charity Shield was not held. | — |
| 2003/04 | - | - The Charity Shield was not held. | — |
| 2002/03 | - | - The Charity Shield was not held. | — |
| 2001/02 | - | - The Charity Shield was not held. | — |
| 2000/01 | - | - The Charity Shield was not held. | — |
| 1999/00 Irish League Charity Shield | Linfield FC | Glentoran FC Final: 2-0. | — |
| 1998/99 Irish League Charity Shield | Portadown FC | Glentoran FC Final: 1-2. | — |
| 1997/98 Irish League Charity Shield | Cliftonville FC | Glentoran FC Final: 1-0. | — |
| 1996/97 Irish League Charity Shield | - | - The Charity Shield was not held. | — |
| 1995/96 Irish League Charity Shield | - | - The Charity Shield was not held. | — |
| 1994/95 Irish League Charity Shield | - | - The Charity Shield was not held. | — |
| 1993/94 Irish League Charity Shield | Linfield FC | Bangor FC Final: 2-0. | — |
| 1992/93 Irish League Charity Shield | Linfield FC Bangor FC | - 1-1; title shared. | — |
| 1991/92 Irish League Charity Shield | Glentoran FC Glenavon FC | - 1-1; title shared. | — |
