| 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 | 1 | Hearts | 4 | 2 | 2 | 0 | 6 | 3 | +3 | 8 | XWWX | |
| 2 | 1 | Dundee United | 4 | 2 | 1 | 1 | 6 | 4 | +2 | 8 | LWWX | |
| 3 | East Fife | 4 | 2 | 1 | 1 | 5 | 3 | +2 | 8 | XWWL | ||
| 4 | 1 | Stenhousemuir | 4 | 1 | 0 | 3 | 4 | 6 | -2 | 3 | WLLL | |
| 5 | 1 | Cowdenbeath | 4 | 1 | 0 | 3 | 2 | 7 | -5 | 3 | LLLW | |
| Saturday, 27 July 2019 | |||||
| 5 | East Fife | 1-1 | Hearts | ||
| 54 | Duggan | 15 | Walker | ||
| 5 | Stenhousemuir | 2-0 | Cowdenbeath | ||
| 33 | McGuigan | ||||
| 85(og) | Todd | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 4 | 4 | 0 | 0 | 12 | 2 | +10 | 12 | WWWW | ||
| 2 | Forfar Athletic | 4 | 3 | 0 | 1 | 9 | 4 | +5 | 9 | WLWW | ||
| 3 | 1 | Montrose | 4 | 1 | 1 | 2 | 4 | 9 | -5 | 5 | XLWL | |
| 4 | 1 | St.Johnstone | 4 | 1 | 0 | 3 | 6 | 5 | +1 | 3 | LWLL | |
| 5 | Brechin City | 4 | 0 | 1 | 3 | 1 | 12 | -11 | 1 | XLLL | ||
| Saturday, 27 July 2019 | |||||
| 5 | Brechin City | 1-1 | Montrose | ||
| 73 | Reekie | 57 | Campbell | ||
| 5 | Forfar Athletic | 2-1 | St.Johnstone | ||
| 2 | Tapping | 65 | Kennedy | ||
| 53 | Forbes | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Hibernian | 4 | 3 | 1 | 0 | 8 | 1 | +7 | 11 | WWWX | ||
| 2 | 2 | Alloa Athletic | 4 | 2 | 1 | 1 | 8 | 8 | +0 | 7 | WWLX | |
| 3 | 1 | Arbroath | 4 | 2 | 0 | 2 | 10 | 8 | +2 | 6 | LLWW | |
| 4 | 1 | Elgin City | 4 | 1 | 1 | 2 | 7 | 7 | +0 | 5 | LWXL | |
| 5 | Stirling Albion | 4 | 0 | 1 | 3 | 3 | 12 | -9 | 1 | LLLX | ||
| Friday, 26 July 2019 | |||||
| 5 | Elgin City | 0-2 | Hibernian | ||
| 10 | Newell | ||||
| 62 | Kamberi | ||||
| Saturday, 27 July 2019 | |||||
| 5 | Arbroath | 2-3 | Alloa Athletic | ||
| 18 | Linn | 18 | Buchanan | ||
| 74 | Thomson | 51 | Trouten | ||
| 78 | Trouten | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dundee | 4 | 2 | 2 | 0 | 4 | 0 | +4 | 10 | WOOW | |
| 2 | 1 | Inverness CT | 4 | 2 | 1 | 1 | 7 | 4 | +3 | 7 | LWWO | |
| 3 | Peterhead | 4 | 1 | 2 | 1 | 3 | 4 | -1 | 6 | LOOW | ||
| 4 | 1 | Cove Rangers | 4 | 1 | 1 | 2 | 6 | 5 | +1 | 4 | WLOL | |
| 5 | 1 | Raith Rovers | 4 | 1 | 0 | 3 | 4 | 11 | -7 | 3 | LWLL | |
| Saturday, 27 July 2019 | |||||
| 5 | Cove Rangers | 3-0 | Raith Rovers | ||
| 45 | Masson | ||||
| 52 | Antoniazzi | ||||
| 73 | Glass | ||||
| Sunday, 28 July 2019 | |||||
| 5 | Dundee | 1-0 | Inverness CT | ||
| 33 | Johnson | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 4 | 4 | 0 | 0 | 13 | 0 | +13 | 12 | WWWW | ||
| 2 | Morton | 4 | 2 | 1 | 1 | 14 | 8 | +6 | 8 | XWLW | ||
| 3 | Queen of the South | 4 | 1 | 2 | 1 | 10 | 10 | +0 | 6 | XWXL | ||
| 4 | Dumbarton | 4 | 1 | 0 | 3 | 3 | 12 | -9 | 3 | LLLW | ||
| 5 | Annan Athletic | 4 | 0 | 1 | 3 | 3 | 13 | -10 | 1 | LLXL | ||
| Saturday, 27 July 2019 | |||||
| 5 | Motherwell | 4-0 | Annan Athletic | ||
| 20 | Donnelly | ||||
| 44 | Polworth | ||||
| 89 | Donnelly | ||||
| 90 | Scott | ||||
| 5 | Morton | 3-3 | Queen of the South | ||
| 31 | Sutton | 4 | Kilday | ||
| 45(p) | Cadden | 62(og) | McAlister | ||
| 56 | McHugh | 78 | Semple | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 4 | 3 | 1 | 0 | 8 | 5 | +3 | 10 | WXWW | ||
| 2 | Hamilton | 4 | 2 | 2 | 0 | 8 | 5 | +3 | 9 | WXWO | ||
| 3 | Airdrieonians | 4 | 1 | 1 | 2 | 7 | 8 | -1 | 5 | LXWL | ||
| 4 | Queen's Park | 4 | 0 | 3 | 1 | 4 | 5 | -1 | 5 | XXLO | ||
| 5 | Clyde | 4 | 0 | 1 | 3 | 6 | 10 | -4 | 1 | XLLL | ||
| Saturday, 27 July 2019 | |||||
| 5 | Airdrieonians | 2-3 | Hamilton | ||
| 10 | Smith | 48(p) | Cunningham | ||
| 24 | Roy | 60(p) | Cunningham | ||
| 89 | Ogboe | ||||
| Sunday, 28 July 2019 | |||||
| 5 | Queen's Park | 1-1 | Clyde | ||
| 86(og) | Howie | 23 | Smith | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 4 | 3 | 1 | 0 | 10 | 3 | +7 | 11 | WWWX | ||
| 2 | 1 | Ayr United | 4 | 2 | 1 | 1 | 12 | 5 | +7 | 7 | XWLW | |
| 3 | 1 | Falkirk | 4 | 2 | 1 | 1 | 6 | 3 | +3 | 7 | WLWX | |
| 4 | Stranraer | 4 | 1 | 1 | 2 | 9 | 5 | +4 | 5 | XLWL | ||
| 5 | Berwick Rangers | 4 | 0 | 0 | 4 | 0 | 21 | -21 | 0 | LLLL | ||
| Saturday, 27 July 2019 | |||||
| 5 | Ayr United | 2-2 | Stranraer | ||
| 2 | Moffat | 42 | Cummins | ||
| 44 | Kelly | 86 | Cummins | ||
| 5 | Livingston | 5-0 | Berwick Rangers | ||
| 2 | Lamie | ||||
| 16 | Sibbald | ||||
| 24 | Lithgow | ||||
| 81 | Lamie | ||||
| 84 | Sibbald | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dunfermline | 4 | 3 | 0 | 1 | 13 | 3 | +10 | 9 | WLWW | ||
| 2 | 2 | Albion Rovers | 4 | 2 | 1 | 1 | 3 | 7 | -4 | 7 | WOLW | |
| 3 | 1 | St.Mirren | 4 | 1 | 2 | 1 | 3 | 3 | +0 | 6 | OOWL | |
| 4 | 1 | East Kilbride | 4 | 1 | 1 | 2 | 1 | 5 | -4 | 5 | LWOL | |
| 5 | FC Edinburgh | 4 | 1 | 0 | 3 | 2 | 4 | -2 | 3 | LLWL | ||
| Saturday, 27 July 2019 | |||||
| 5 | Dunfermline | 4-0 | East Kilbride | ||
| 3 | Nisbet | ||||
| 7 | Coley | ||||
| 16 | Beadling | ||||
| 50 | Nisbet | ||||
| 5 | Albion Rovers | 2-1 | FC Edinburgh | ||
| 8 | East | 62(p) | Henderson | ||
| 54 | Paterson | ||||
| 5 | +2 | Kevin NISBET (Dunfermline) |
| 4 | Ross STEWART (Ross County) | |
| Shane SUTHERLAND (Elgin City) | ||
| +2 | Ross CUNNINGHAM (Hamilton, 2p) | |
| Billy McKAY (Ross County) | ||
| +2 | Liam DONNELLY (Motherwell, 1p) | |
| 3 | +1 | Nicky CADDEN (Morton, 1p) |
| Luke McCOWAN (Ayr United) | ||
| +2 | Ricky LAMIE (Livingston) | |
| Declan McMANUS (Falkirk) | ||
| +1 | Michael MOFFAT (Ayr United) | |
| Craig HALKETT (Hearts) | ||
| Shea GORDON (Partick Thistle) | ||
| +1 | Alistair ROY (Airdrieonians, 1p) | |
| +1 | Liam BUCHANAN (Alloa Athletic) | |
| +2 | Alan TROUTEN (Alloa Athletic) | |
| +1 | James SCOTT (Motherwell) | |
| Michael TRAVIS (Forfar Athletic) |