2018-19 IFA Challenge Cup
First Round
| 11-Aug | Man City | 2-4 | Rochdale |
| 08-Sep | Bury B | 6-2 | Queens Park |
| 22-Sep | Bury A | 4-0 | Dunfermline |
| 6-Oct | West Ham | 4-0 | Alloa |
| 13-Oct | Preston NE | 3-2 | Hearts |
| 13-Oct | Livingston GS | 5-2 | Salford |
| 03-Nov | Motherwell | 2-5 | Troon |
| 03-Nov | West Brom | 3-2 | Halifax |
| N/A | Airdrie | w-0 | Man Utd |
| N/A | Rotherham | w-0 | Wrexham |
| N/A | Stirling | v | Ayr |
| N/A | Millwall | v | Bye |
| N/A | Celtic | v | Bye |
| N/A | Gillingham | v | Bye |
| N/A | St Johnstone | v | Bye |
| N/A | Watford | v | Bye |
Second Round
| Date | Home | v | Away |
|---|---|---|---|
| 05-Jan | Airdrie | 0-4 | Livingston GS |
| 05-Jan | Ayr | 2-0 | Bury B |
| 23-Feb | Troon | 8-0 | Celtic |
| 23-Feb | Millwall | 5-2 | Preston NE |
| 23-Feb | St Johnstone | 6-1 | West Ham |
| 09-Mar | Rochdale | 6-1 | Watford |
| 09-Mar | West Brom | 6-1 | Bury A |
| N/A | Rotherham | w-0 | Gillingham |
Quarter Finals
| Date | Home | v | Away |
|---|---|---|---|
| 13-Apr | Troon | 2-1 | Rochdale |
| 06-Apr | Millwall | 2(4)-(2)2 | Ayr |
| 11-May | Livingston GS | 5-2 | West Brom |
| 13-Apr | Rotherham | 1(6)-(5)1 | St Johnstone |
Semi Finals
| Date | Home | v | Away |
|---|---|---|---|
| 1-Jun | Troon | 7-1 | Millwall |
| Date | Livingston GS | v | Rotherham |
Final
Troon 5-3 Rotherham
Goalscorers
| 0 | First Name | Second Name | Club | Cup Goals |
| 1 | Jonny | Duff | Troon | 5 |
| Grant | Valentine | Troon | ||
| 2 | Matt | Gallagher | St Johnstone | 4 |
| 3 | Brett | Hardman | Rochdale | 3 |
| 4 | Kyle | Davies | Rochdale | 2 |
| Andy | Dodwell | Preston NE | ||
| Mark | Eccles | Bury A | ||
| James | Hardman | Rochdale | ||
| Nathan | Hardman | Rochdale | ||
| Danny | Lee | Salford C | ||
| Chris | Lees | Livingston GS | ||
| Chris | McGrail | Preston NE | ||
| Jamie | Pav | Manchester C | ||
| Dougie | Sedgeworth | Troon | ||
| Ben | Wallace | West Brom |