2019-20 IFA Challenge Cup
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 | v | |||
| TBC | Queens Park | v | Watford | ||
| TBC | Ayr | v | St Johnstone |
Final
| Date | Home | v | Away | ||
| TBC | TBC | v | TBC |
Goalscorers
| First Name | Second Name | Club | Cup Goals |
| Kyle | Davies | Rochdale | 3 |
| Adam | Gallichan | Watford | 2 |
| James | Hardman | Rochdale | 2 |
| Craig | Keatings | Motherwell | 2 |
| Kieron | Murphy | Preston NE | 2 |
| Sam | Norris | Bury | 2 |
| Jamie | Bates | Bury | 1 |
| Chris | Chambers | Preston NE | 1 |
| Ross | Dunbar | Queens Park | 1 |
| Adam | Ellsworth | Queens Park | 1 |
| Ben | Fawles | Halifax | 1 |
| Jordan | Foster | Ayr | 1 |
| Brett | Hardman | Rochdale | 1 |
| Scott | MacRae | Queens Park | 1 |
| Pete | Noble | Ayr | 1 |
| Ross | Pate | Motherwell | 1 |
| Mark | Pettigrew | Ayr | 1 |
| Sandy | Reid | Ayr | 1 |
| Jordi | Singleton | Preston NE | 1 |
| Graeme | Tobin | Bury | 1 |
| Luke | Walsh | Rochdale | 1 |
| Charlie | Wood | Watford | 1 |
| Aaron | Woodruff | Preston NE | 1 |