| Iirimaa Leinster Senior League | 2021/07/09 18:30 | Portlaoise AFC v St. Kevin''s Boys | L | 2-1 |
| Iirimaa Leinster Senior League | 2022/04/23 11:00 | Columbas Rovers v St. Kevin''s Boys | D | 1-1 |
| Iirimaa Leinster Senior League | 2021/10/29 19:00 | St. Kevin''s Boys v St Francis FC | D | 0-0 |
| Iirimaa Leinster Senior League | 2021/09/03 19:00 | St. Kevin''s Boys v Drumcondra | W | 3-0 |
| Iirimaa FAI Cup | 2021/07/23 19:00 | St. Kevin''s Boys v Kilnamanagh AFC | L | 1-4 |
| Iirimaa Leinster Senior League | 2021/07/09 18:30 | Portlaoise AFC v St. Kevin''s Boys | L | 2-1 |
| Iirimaa Leinster Senior League | 2020/08/13 18:00 | Sacred Heart Firhouse Clover v St. Kevin''s Boys | L | 2-0 |
| Iirimaa Leinster Senior League | 2020/07/30 19:00 | St Francis FC v St. Kevin''s Boys | W | 3-4 |
| Iirimaa Leinster Senior League | 2019/01/14 19:45 | Beggsboro AFC v St. Kevin''s Boys | W | 3-4 |
| Iirimaa Leinster Senior League | 2022/04/10 10:00 | Drumcondra v Portlaoise AFC | D | 2-2 |
| Iirimaa Leinster Senior League | 2022/02/04 19:30 | Portlaoise AFC v Templeogue United FC | W | 2-1 |
| Iirimaa Leinster Senior League | 2022/01/28 19:30 | Portlaoise AFC v Tullamore Town | W | 3-2 |
| Iirimaa Leinster Senior League | 2022/01/22 12:00 | UCD AFC v Portlaoise AFC | L | 1-0 |
| Iirimaa Amateur Cup | 2022/01/21 19:30 | Portlaoise AFC v Ayrfield United | W | 4-1 |
| Iirimaa Leinster Senior League | 2022/01/15 15:00 | Greystones v Portlaoise AFC | W | 0-2 |
| Iirimaa Leinster Senior League | 2021/10/22 18:30 | Portlaoise AFC v Newtown Rangers AFC | W | 2-0 |
| Iirimaa Leinster Senior League | 2021/10/08 18:30 | Portlaoise AFC v Drumcondra | W | 4-1 |