August 2019
| Mon 26 Aug - 2:00 pm | Kilmac Stadium at Dens Park | Dundee Reserves |  |
2 - 4 |  |
Celtic | Reserve Cup | Match Report |
October 2019
| Mon 21 Oct - 2:00 pm | Cappielow | Greenock Morton |  |
0 - 1 | |
Dundee Reserves | Reserve Cup | Match Report |
December 2019
| Mon 2 Dec - 1:00 pm | Station Park | Dundee Reserves | |
1 - 1 |  |
Dunfermline Athletic | Reserve Cup | Match Report |
January 2020
| Mon 27 Jan - 2:00 pm | Broadwood | Motherwell |  |
2 - 1 | |
Dundee Reserves | Reserve Cup | Match Report |
