| 1 | Sun 8 Sep 2019 | 2-1 v DundeeDundee 1-2 Elgin City | Tunnock's Challenge Cup Third Round |
| 2 | Sat 14 Sep 2019 | 0-1 v Stirling AlbionStirling Albion 1-0 Elgin City | Ladbrokes League Two |
| 3 | Sat 21 Sep 2019 | 0-2 v Cove RangersElgin City 0-2 Cove Rangers | Ladbrokes League Two |
| 4 | Sat 28 Sep 2019 | 1-2 v Brechin CityBrechin City 2-1 Elgin City | Ladbrokes League Two |
| 5 | Sat 5 Oct 2019 | 3-1 v Albion RoversAlbion Rovers 1-3 Elgin City | Ladbrokes League Two |
| 6 | Sat 12 Oct 2019 | 2-0 v AirdrieoniansAirdrieonians 0-2 Elgin City | Tunnock's Challenge Cup Quarter Final |
| 7 | Sat 26 Oct 2019 | 3-1 v Queens ParkElgin City 3-1 Queens Park | Ladbrokes League Two |
| 8 | Sat 2 Nov 2019 | 4-0 v Annan AthleticElgin City 4-0 Annan Athletic | Ladbrokes League Two |
| 9 | Sat 9 Nov 2019 | 1-1 v Edinburgh CityEdinburgh City 1-1 Elgin City | Ladbrokes League Two |
| 10 | Fri 15 Nov 2019 | 2-3 v Raith RoversRaith Rovers 3-2 Elgin City | Tunnock's Challenge Cup Quarter Final |
| 11 | Sat 30 Nov 2019 | 1-2 v Stirling AlbionElgin City 1-2 Stirling Albion | Ladbrokes League Two |
| 12 | Tue 3 Dec 2019 | 2-2 v StenhousemuirStenhousemuir 2-2 Elgin City | Ladbrokes League Two |
| 13 | Sat 7 Dec 2019 | 0-0 v CowdenbeathCowdenbeath 0-0 Elgin City | Ladbrokes League Two |
| 14 | Sat 14 Dec 2019 | 2-2 v Albion RoversElgin City 2-2 Albion Rovers | Ladbrokes League Two |
| 15 | Sat 21 Dec 2019 | 3-1 v Brechin CityElgin City 3-1 Brechin City | Ladbrokes League Two |
| 16 | Sat 28 Dec 2019 | 0-2 v Cove RangersCove Rangers 2-0 Elgin City | Ladbrokes League Two |
| 17 | Sat 25 Jan 2020 | 2-1 v Stirling AlbionStirling Albion 1-2 Elgin City | Ladbrokes League Two |
| 18 | Sat 15 Feb 2020 | 0-2 v Queens ParkQueens Park 2-0 Elgin City | Ladbrokes League Two |
| 19 | Sat 29 Feb 2020 | 2-1 v Albion RoversAlbion Rovers 1-2 Elgin City | Ladbrokes League Two |
| 20 | Sat 7 Mar 2020 | 3-1 v Stirling AlbionElgin City 3-1 Stirling Albion | Ladbrokes League Two |
| 21 | Tue 10 Mar 2020 | 3-2 v CowdenbeathElgin City 3-2 Cowdenbeath | Ladbrokes League Two |
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