| 1 | Sat 13 Jul 2019 | 1-2 v PeterheadPeterhead 2-1 Cove Rangers | Betfred Cup Group D |
| 2 | Sat 10 Aug 2019 | 4-4 v Albion RoversAlbion Rovers 4-4 Cove Rangers | Ladbrokes League Two |
| 3 | Tue 13 Aug 2019 | 2-1 v Brora RangersBrora Rangers 1-2 Cove Rangers | Tunnock's Challenge Cup Second Round |
| 4 | Sat 24 Aug 2019 | 2-1 v Stirling AlbionStirling Albion 1-2 Cove Rangers | Ladbrokes League Two |
| 5 | Sat 31 Aug 2019 | 3-0 v Queens ParkCove Rangers 3-0 Queens Park | Ladbrokes League Two |
| 6 | Sat 7 Sep 2019 | 0-1 v Connah's Quay NomadsConnah's Quay Nomads 1-0 Cove Rangers | Tunnock's Challenge Cup Third Round |
| 7 | Sat 14 Sep 2019 | 4-2 v Brechin CityBrechin City 2-4 Cove Rangers | Ladbrokes League Two |
| 8 | Sat 21 Sep 2019 | 2-0 v Elgin CityElgin City 0-2 Cove Rangers | Ladbrokes League Two |
| 9 | Sat 28 Sep 2019 | 3-0 v Annan AthleticCove Rangers 3-0 Annan Athletic | Ladbrokes League Two |
| 10 | Sat 5 Oct 2019 | 2-3 v StenhousemuirStenhousemuir 3-2 Cove Rangers | Ladbrokes League Two |
| 11 | Tue 29 Oct 2019 | 3-0 v Albion RoversCove Rangers 3-0 Albion Rovers | Ladbrokes League Two |
| 12 | Sat 2 Nov 2019 | 3-1 v CowdenbeathCowdenbeath 1-3 Cove Rangers | Ladbrokes League Two |
| 13 | Sat 9 Nov 2019 | 1-0 v Stirling AlbionCove Rangers 1-0 Stirling Albion | Ladbrokes League Two |
| 14 | Sat 16 Nov 2019 | 3-0 v Brechin CityCove Rangers 3-0 Brechin City | Ladbrokes League Two |
| 15 | Sat 30 Nov 2019 | 1-6 v Annan AthleticAnnan Athletic 6-1 Cove Rangers | Ladbrokes League Two |
| 16 | Sat 7 Dec 2019 | 1-2 v Edinburgh CityEdinburgh City 2-1 Cove Rangers | Ladbrokes League Two |
| 17 | Sat 21 Dec 2019 | 3-1 v Queens ParkQueens Park 1-3 Cove Rangers | Ladbrokes League Two |
| 18 | Sat 28 Dec 2019 | 2-0 v Elgin CityCove Rangers 2-0 Elgin City | Ladbrokes League Two |
| 19 | Sat 4 Jan 2020 | 5-1 v Brechin CityBrechin City 1-5 Cove Rangers | Ladbrokes League Two |
| 20 | Sat 25 Jan 2020 | 2-0 v Annan AthleticCove Rangers 2-0 Annan Athletic | Ladbrokes League Two |
| 21 | Sat 1 Feb 2020 | 2-2 v Albion RoversAlbion Rovers 2-2 Cove Rangers | Ladbrokes League Two |
| 22 | Sat 8 Feb 2020 | 0-3 v Elgin CityElgin City 3-0 Cove Rangers | Ladbrokes League Two |
| 23 | Sat 15 Feb 2020 | 2-1 v Edinburgh CityCove Rangers 2-1 Edinburgh City | Ladbrokes League Two |
| 24 | Sat 22 Feb 2020 | 2-0 v Queens ParkCove Rangers 2-0 Queens Park | Ladbrokes League Two |
| 25 | Sat 29 Feb 2020 | 3-0 v StenhousemuirStenhousemuir 0-3 Cove Rangers | Ladbrokes League Two |
| 26 | Sat 7 Mar 2020 | 3-2 v Brechin CityCove Rangers 3-2 Brechin City | Ladbrokes League Two |
| 27 | Tue 10 Mar 2020 | 7-1 v Stirling AlbionStirling Albion 1-7 Cove Rangers | Ladbrokes League Two |
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