Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 04.01.2020 |  | Matchday 20 | Dundee FC - Inverness | Dun - INV | 0:2 | 5.040 |
| 18.01.2020 |  | 4. Round | Dundee FC - Motherwell | Dun - MOT | 0:3 | 2.407 |
| 01.02.2020 | | Matchday 23 | Dundee Utd - Arbroath FC | DUN - Arb | 0:1 | 8.056 |
| 08.02.2020 | | Matchday 24 | Dundee FC - Partick Thistle | Dun - PT | 2:0 | 4.816 |
| 03.03.2020 | | Matchday 27 | Dundee FC - Alloa Ath. | Dun - ALL | 0:0 | 4.356 |
| 10.03.2020 | | Matchday 21 | Dundee FC - Ayr United | Dun - | 2:0 | 4.670 |
| 06.10.2020 |  | Group B | Dundee FC - Forfar Athletic | Dun - FOR | 3:0 | |
| 24.10.2020 | | Matchday 2 | Dundee FC - Morton | Dun - Mor | 1:0 | |
| 31.10.2020 | | Matchday 3 | Dundee FC - Raith Rovers | Dun - Rai | 1:1 | |
| 10.11.2020 | | Group B | Dundee FC - Cove Rangers | Dun - | 3:0 | Unter Ausschluss der Öffentlichkeit. |
| 05.12.2020 | | Matchday 6 | Dundee FC - Arbroath FC | Dun - Arb | 1:0 | |
| 19.12.2020 | | Matchday 8 | Dundee FC - Dunfermline | Dun - DUN | 3:3 | |
| 29.12.2020 | | Matchday 10 | Dundee FC - Alloa Ath. | Dun - ALL | 3:1 |