| ROUND | R1 | R2 | R3 | R4 | QF | SF | F | ||
| N | S | N | S | ||||||
| Season archive |
| Friday, 11 October 2019 | ||||||
| r4 | Stenhousemuir | 3-2 | Waterford | |||
| 30 | McLaughlin | 24 | Fitzgerald | |||
| 61 | Hopkirk | 74 | O'Connor | |||
| 90 | McGuigan | |||||
| Saturday, 12 October 2019 | ||||||
| r4 | Wrexham | 4-1 | St.Mirren U20 | |||
| 46 | Redmond | 68 | Henderson | |||
| 55(p) | McIntosh | |||||
| 73 | McIntosh | |||||
| 89 | Tollitt | |||||
| r4 | Raith Rovers | 3-1 | Glenavon | |||
| 15 | Bowie | 24 | Marshall | |||
| 32 | Armstrong | |||||
| 90 | Allan | |||||
| r4 | Airdrieonians | 0-2 | Elgin City | |||
| 88 | Hester | |||||
| 90(p) | Sutherland | |||||
| r4 | Partick Thistle | 2-0 | Connah's Quay | |||
| 34 | De Vita | |||||
| 77 | Penrice | |||||
| r4 | Inverness CT | 3-0 | Alloa Athletic | |||
| 42 | Curry | |||||
| 64 | Trafford | |||||
| 88 | Machado | |||||
| r4 | Arbroath | 0-2 | Clyde | |||
| 9 | Johnston | |||||
| 68 | Howie | |||||
| Tuesday, 29 October 2019 | ||||||
| r4 | Solihull Moors | 3-3 | Rangers B | p3-4 | ||
| 8 | Howe | 11 | Barjonas | |||
| 36 | Yussuf | 69 | Grezda | |||
| 60 | Carter | 84 | Grezda | |||
| 6 | +1 | Kane HESTER (Elgin City) |
| 4 | +1 | Shane SUTHERLAND (Elgin City) |
| 3 | Scott REEKIE (Brechin City) | |
| +1 | Lewis ALLAN (Raith Rovers) | |
| Aidan KEENA (Hearts B) | ||
| 2 | +2 | Eros GREZDA (Rangers B) |
| +2 | Leighton McINTOSH (Wrexham) | |
| Calum GALLAGHER (Airdrieonians) | ||
| Mark GALLAGHER (Ross County U20) | ||
| Ryan WATTERS (Stenhousemuir) | ||
| Josh McPAKE (Rangers B) | ||
| Andy WINTER (Hamilton U20) | ||
| David GOODWILLIE (Clyde) | ||
| Kyle MacLEOD (Brora Rangers) | ||
| +1 | Rhys MARSHALL (Glenavon) | |
| +1 | Jamie BARJONAS (Rangers B) | |
| Martin McNIFF (Clyde) | ||
| Davis KEILLOR-DUNN (Ross County U20) |