 Kelty Hearts |
| 20-Oct-2018 | SFAC (r2) | Peterhead | 3-2 | Kelty Hearts |
| 06-Aug-2019 | ChC (r1ss) | Kelty Hearts | 4-0 | Kilmarnock U20 |
| 13-Aug-2019 | ChC (r2ss) | Annan Athletic | 1-1 | Kelty Hearts |
| 07-Sep-2019 | ChC (r3) | Kelty Hearts | 1-1 |  Solihull Moors |
| 07-Oct-2020 | LC (r1gr1) | Kelty Hearts | 1-2 | St.Johnstone |
| 13-Oct-2020 | LC (r1gr3) | Dundee United | 1-0 | Kelty Hearts |
| 10-Nov-2020 | LC (r1gr4) | Kelty Hearts | 1-1 | Peterhead |
| 14-Nov-2020 | LC (r1gr5) | Brechin City | 0-2 | Kelty Hearts |
| 09-Jan-2021 | SFAC (r2) | Kelty Hearts | 2-2 | Stranraer |
