Due to the Covid-19 pandemic, the 2019-20 IFA Challenge Cup was completed in Summer 2021.
First Round
| Date | Home | v | Away | ||
| Hearts | W/O | v | Troon | ||
| 21-Sep | Celtic | 4 | v | 0 | Livingston GS |
| 19-Oct | Motherwell | 3 (3) | v | 3 (4) | Queens Park |
| 09-Nov | Salford City | 1 | v | 5 | Preston |
Second Round
| Date | Home | v | Away | ||
| Alloa | W/O | v | Manchester City | ||
| v | Bye | Watford | |||
| Celtic | v | Bye | Preston | ||
| 7-Sep | Bury | 4 (4) | v | 4 (5) | Ayr |
| 28-Sep | Rochdale | 7 | v | 1 | Stirling Albion |
| 30-Nov | AFC Halifax | 1 | v | 3 | Queens Park |
| 07-Dec | Hearts | 2 | v | 3 | Dunfermline |
| 11-Jan | St Johnstone | 5 | v | 4 | Airdrie |
Quarter Finals
| Date | Home | v | Away | ||
| 25-Jan | Queens Park | 1 (4) | v | 1 (2) | Rochdale |
| 01-Feb | Watford | 3 | v | 1 | Dunfermline |
| 22-Feb | Preston | 1 | v | 4 | St Johnstone |
| Alloa | v | W/O | Ayr |
Semi Finals
| Date | Neutral Venues | ||||
| 26-Jun-21 | Queens Park | 3 | v | 8 | Watford |
| 12-Jun-21 | Ayr | 1 | v | 3 | St Johnstone |
Final
| Date | Nottingham | ||||
| 16-Jul-21 | St Johnstone | v | W/O | Watford |