| ROUND | R1 | R2 | QF | SF | F | ||||
| r1 | r2 | r3 | r4 | r5 | |||||
| Season archive |
| Group A | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Cowdenbeath | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | |
| 2 | 2 | Dundee United | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | |
| 3 | 1 | Hearts | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| 4 | Stenhousemuir | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 5 | East Fife | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| Friday, 12 July 2019 | |||||
| 1 | Hearts | 1-1 | Dundee United | ||
| 44 | Irving | 9 | Shankland | ||
| Saturday, 13 July 2019 | |||||
| 1 | Cowdenbeath | 2-0 | East Fife | ||
| 17 | Buchanan | ||||
| 27 | Taylor | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 1 | 1 | 0 | 0 | 4 | 1 | +3 | 3 | W--- | ||
| 2 | 2 | Forfar Athletic | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 3 | 2 | St.Johnstone | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | 1 | Montrose | 1 | 0 | 0 | 1 | 1 | 4 | -3 | 0 | L--- | |
| 5 | 2 | Brechin City | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| Saturday, 13 July 2019 | |||||
| 1 | Ross County | 4-1 | Montrose | ||
| 7 | Mullin | 51 | Allan | ||
| 13 | Stewart | ||||
| 46 | Stewart | ||||
| 85 | McKay | ||||
| 1 | Forfar Athletic | 3-0 | Brechin City | ||
| 20 | Travis | ||||
| 45 | Kirkpatrick | ||||
| 65 | Jackson | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Arbroath | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | |
| 2 | 1 | Hibernian | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | |
| 3 | 1 | Stirling Albion | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| 4 | 1 | Alloa Athletic | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 5 | Elgin City | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| Saturday, 13 July 2019 | |||||
| 1 | Stirling Albion | 1-1 | Hibernian | ||
| 70 | Wilson | 44(p) | Allan | ||
| 1 | Arbroath | 2-1 | Elgin City | ||
| 44 | Kader | 29 | Sutherland | ||
| 90 | Doris | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dundee | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 2 | 3 | Peterhead | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | |
| 3 | 2 | Inverness CT | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 4 | Cove Rangers | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| 5 | Raith Rovers | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| Saturday, 13 July 2019 | |||||
| 1 | Raith Rovers | 0-3 | Dundee | ||
| 14 | Nelson | ||||
| 29(p) | Nelson | ||||
| 75 | Curran | ||||
| 1 | Peterhead | 2-1 | Cove Rangers | ||
| 20 | Lyle | 14(p) | Masson | ||
| 39(p) | McAllister | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | ||
| 2 | 1 | Dumbarton | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | Morton | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 4 | Annan Athletic | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| 5 | 3 | Queen of the South | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | |
| Saturday, 13 July 2019 | |||||
| 1 | Queen of the South | 0-3 | Motherwell | ||
| 71(p) | Donnelly | ||||
| 90 | Seedorf | ||||
| 90 | Hylton | ||||
| 1 | Annan Athletic | 0-1 | Dumbarton | ||
| 63 | Tierney | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Partick Thistle | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 2 | 2 | Queen's Park | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 2 | O--- | |
| 3 | Hamilton | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 1 | O--- | ||
| 4 | Clyde | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 5 | 3 | Airdrieonians | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Saturday, 13 July 2019 | |||||
| 1 | Partick Thistle | 1-0 | Airdrieonians | ||
| 66(og) | Crighton | ||||
| 1 | Hamilton | 0-0 | Queen's Park | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ayr United | 1 | 1 | 0 | 0 | 7 | 0 | +7 | 3 | W--- | ||
| 2 | 1 | Livingston | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | |
| 3 | 1 | Falkirk | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| 4 | 1 | Stranraer | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | |
| 5 | Berwick Rangers | 1 | 0 | 0 | 1 | 0 | 7 | -7 | 0 | L--- | ||
| Saturday, 13 July 2019 | |||||
| 1 | Falkirk | 1-1 | Livingston | ||
| 90 | Sammon | 36 | Dykes | ||
| 1 | Berwick Rangers | 0-7 | Ayr United | ||
| 21 | Moffat | ||||
| 26 | McCowan | ||||
| 35 | Doolan | ||||
| 36 | Moffat | ||||
| 42 | McGuffie | ||||
| 70 | McCowan | ||||
| 86 | Doolan | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dunfermline | 1 | 1 | 0 | 0 | 3 | 2 | +1 | 3 | W--- | ||
| 2 | 3 | Albion Rovers | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | FC Edinburgh | 0 | 0 | 0 | 0 | 0 | 0 | +0 | 0 | ---- | ||
| 4 | 2 | St.Mirren | 1 | 0 | 0 | 1 | 2 | 3 | -1 | 0 | L--- | |
| 5 | 1 | East Kilbride | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Saturday, 13 July 2019 | |||||
| 1 | East Kilbride | 0-1 | Albion Rovers | ||
| 25 | Stewart | ||||
| Sunday, 14 July 2019 | |||||
| 1 | St.Mirren | 2-3 | Dunfermline | ||
| 63 | Cooke | 18 | Dow | ||
| 65 | Mullen | 24 | Ryan | ||
| 40 | Beadling | ||||
| 2 | +2 | Kris DOOLAN (Ayr United) |
| +2 | Ross STEWART (Ross County) | |
| +2 | Andrew NELSON (Dundee, 1p) | |
| +2 | Luke McCOWAN (Ayr United) | |
| +2 | Michael MOFFAT (Ayr United) |