| 1 | Sat 22 Dec 2018 | 4-0 v Queens ParkQueens Park 0-4 Elgin City |
| 2 | Sat 29 Dec 2018 | 0-3 v PeterheadElgin City 0-3 Peterhead |
| 3 | Sat 5 Jan 2019 | 0-2 v Annan AthleticAnnan Athletic 2-0 Elgin City |
| 4 | Sat 12 Jan 2019 | 1-4 v CowdenbeathElgin City 1-4 Cowdenbeath |
| 5 | Sat 26 Jan 2019 | 3-3 v Edinburgh CityElgin City 3-3 Edinburgh City |
| 6 | Sat 9 Feb 2019 | 3-0 v Albion RoversAlbion Rovers 0-3 Elgin City |
| 7 | Sat 16 Feb 2019 | 3-2 v Stirling AlbionElgin City 3-2 Stirling Albion |
| 8 | Sat 23 Feb 2019 | 3-0 v Berwick RangersBerwick Rangers 0-3 Elgin City |
| 9 | Tue 26 Feb 2019 | 2-2 v Queens ParkElgin City 2-2 Queens Park |
| 10 | Sat 2 Mar 2019 | 0-1 v PeterheadPeterhead 1-0 Elgin City |
| 11 | Sat 9 Mar 2019 | 2-1 v ClydeElgin City 2-1 Clyde |
| 12 | Sat 16 Mar 2019 | 1-4 v Queens ParkQueens Park 4-1 Elgin City |
| 13 | Tue 19 Mar 2019 | 0-2 v ClydeClyde 2-0 Elgin City |
| 14 | Sat 23 Mar 2019 | 0-2 v Albion RoversElgin City 0-2 Albion Rovers |
| 15 | Sat 30 Mar 2019 | 0-1 v Annan AthleticElgin City 0-1 Annan Athletic |
| 16 | Sat 6 Apr 2019 | 1-2 v Stirling AlbionStirling Albion 2-1 Elgin City |
| 17 | Sat 13 Apr 2019 | 1-2 v CowdenbeathCowdenbeath 2-1 Elgin City |
| 18 | Sat 20 Apr 2019 | 1-2 v PeterheadElgin City 1-2 Peterhead |
| 19 | Sat 27 Apr 2019 | 1-1 v Edinburgh CityEdinburgh City 1-1 Elgin City |
| 20 | Sat 4 May 2019 | 2-0 v Berwick RangersElgin City 2-0 Berwick Rangers |
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