June 2019
| Sat 29 Jun - 1:00 pm | Glebe Park | Brechin City |  |
1 - 2 |  |
Dundee | Pre Season Friendly | Match Report |
July 2019
| Tue 2 Jul - 6:30 pm | Pinatar Arena, Spain | Nottingham Forest |  |
0 - 0 | |
Dundee | Pre Season Friendly | Match Report |
| Tue 9 Jul - 7:45 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 0 |  |
Blackpool | Pre Season Friendly | Match Report |
| Sat 13 Jul - 3:00 pm | Stark's Park | Raith Rovers |  |
0 - 3 | |
Dundee | Betfred Cup | Match Report |
| Wed 17 Jul - 7:45 pm | Balmoral Stadium | Cove Rangers |  |
0 - 0 | |
Dundee | Betfred Cup Group D | Match Report |
| Sat 20 Jul - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 0 |  |
Peterhead | Betfred Cup Group D | Match Report |
| Sun 28 Jul - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 0 |  |
Inverness CT | Betfred Cup | Match Report |
August 2019
| Fri 2 Aug - 7:05 pm | East End Park | Dunfermline Athletic |  |
2 - 2 | |
Dundee | Ladbrokes Championship | Match Report |
| Sat 10 Aug - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 0 |  |
Ayr United | Ladbrokes Championship | Match Report |
| Sun 18 Aug - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 2 |  |
Aberdeen | Betfred Cup | Match Report |
| Sat 24 Aug - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 0 | |
Inverness CT | Ladbrokes Championship | Match Report |
| Fri 30 Aug - 7:45 pm | Tannadice | Dundee United |  |
6 - 2 | |
Dundee | Ladbrokes Championship | Match Report |
September 2019
| Sun 8 Sep - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 2 |  |
Elgin City | Tunnocks Caramel Wafer Challenge Cup | Match Report |
| Sat 14 Sep - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
2 - 1 |  |
Alloa Athletic | Ladbrokes Championship | Match Report |
| Sat 21 Sep - 3:00 pm | Cappielow Park | Greenock Morton |  |
1 - 0 | |
Dundee | Ladbrokes Championship | Match Report |
| Fri 27 Sep - 7:05 pm | Palmerston Park | Queen of the South |  |
1 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
October 2019
| Sat 5 Oct - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
2 - 0 |  |
Arbroath | Ladbrokes Championship | Match Report |
| Sat 19 Oct - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 3 |  |
Partick Thistle | Ladbrokes Championship | Match Report |
| Fri 25 Oct - 7:05 pm | Somerset Park | Ayr United | |
1 - 2 | |
Dundee | Ladbrokes Championship | Match Report |
| Tue 29 Oct - 7:45 pm | The Indodrill Stadium | Alloa Athletic | |
0 - 3 | |
Dundee | Ladbrokes Championship | Match Report |
November 2019
| Fri 1 Nov - 7:05 pm | Kilmac Stadium at Dens Park | Dundee | |
2 - 1 | |
Greenock Morton | Ladbrokes Championship | Match Report |
| Fri 8 Nov - 7:45 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 2 | |
Dundee United | Ladbrokes Championship | Match Report |
| Sat 23 Nov - 3:00 pm | Tulloch Caledonian Stadium | Inverness CT | |
1 - 0 | |
Dundee | Ladbrokes Championship | Match Report |
| Sat 30 Nov - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
1 - 2 | |
Queen of the South | Ladbrokes Championship | Match Report |
December 2019
| Sat 7 Dec - 3:00 pm | Gayfield Park | Arbroath | |
1 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
| Sat 14 Dec - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
4 - 3 | |
Dunfermline Athletic | Ladbrokes Championship | Match Report |
| Sat 21 Dec - 3:00 pm | Energy Check Stadium at Firhill | Partick Thistle | |
0 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
| Fri 27 Dec - 7:45 pm | Tannadice Park | Dundee United | |
1 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
January 2020
| Sat 4 Jan - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 2 | |
Inverness CT | Ladbrokes Championship | Match Report |
| Sat 18 Jan - 7:20 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 3 |  |
Motherwell | William Hill Scottish Cup | Match Report |
| Fri 24 Jan - 7:05 pm | East End Park | Dunfermline Athletic | |
2 - 0 | |
Dundee | Ladbrokes Championship | Match Report |
February 2020
| Sat 1 Feb - 3:00 pm | Cappielow Park | Greenock Morton | |
1 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
| Sat 8 Feb - 3:00 pm | Kilmac Stadium at Dens Park | Dundee | |
2 - 0 | |
Partick Thistle | Ladbrokes Championship | Match Report |
| Sat 22 Feb - 3:00 pm | Palmerston Park | Queen of the South | |
0 - 1 | |
Dundee | Ladbrokes Championship | Match Report |
March 2020
| Tue 3 Mar - 7:45 pm | Kilmac Stadium at Dens Park | Dundee | |
0 - 0 | |
Alloa Athletic | Ladbrokes Championship | Match Report |
| Sat 7 Mar - 3:00 pm | Somerset Park | Ayr United | |
0 - 0 | |
Dundee | Ladbrokes Championship | Match Report |
| Tue 10 Mar - 7:45 pm | Kilmac Stadium at Dens Park | Dundee | |
2 - 0 | |
Ayr United | Ladbrokes Championship | Match Report |
