| 1 | Sat 26 Jan 2019 | 2-3 v Cheltenham TownCheltenham Town 3-2 Macclesfield Town | Sky Bet League Two |
| 2 | Sat 2 Feb 2019 | 1-3 v Mansfield TownMansfield Town 3-1 Macclesfield Town | Sky Bet League Two |
| 3 | Sat 9 Feb 2019 | 3-3 v Crewe AlexandraMacclesfield Town 3-3 Crewe Alexandra | Sky Bet League Two |
| 4 | Sat 16 Feb 2019 | 1-1 v Colchester UnitedMacclesfield Town 1-1 Colchester United | Sky Bet League Two |
| 5 | Sat 23 Feb 2019 | 1-1 v Crawley TownCrawley Town 1-1 Macclesfield Town | Sky Bet League Two |
| 6 | Sat 2 Mar 2019 | 0-3 v BuryBury 3-0 Macclesfield Town | Sky Bet League Two |
| 7 | Sat 9 Mar 2019 | 1-3 v Milton Keynes DonsMacclesfield Town 1-3 Milton Keynes Dons | Sky Bet League Two |
| 8 | Sat 16 Mar 2019 | 2-0 v Yeovil TownYeovil Town 0-2 Macclesfield Town | Sky Bet League Two |
| 9 | Sat 23 Mar 2019 | 2-2 v StevenageMacclesfield Town 2-2 Stevenage | Sky Bet League Two |
| 10 | Sat 30 Mar 2019 | 1-1 v Lincoln CityLincoln City 1-1 Macclesfield Town | Sky Bet League Two |
| 11 | Sat 6 Apr 2019 | 1-1 v MorecambeMacclesfield Town 1-1 Morecambe | Sky Bet League Two |
| 12 | Tue 9 Apr 2019 | 3-2 v Exeter CityMacclesfield Town 3-2 Exeter City | Sky Bet League Two |
| 13 | Sat 13 Apr 2019 | 0-2 v Forest Green RoversForest Green Rovers 2-0 Macclesfield Town | Sky Bet League Two |
| 14 | Fri 19 Apr 2019 | 1-3 v Northampton TownNorthampton Town 3-1 Macclesfield Town | Sky Bet League Two |
| 15 | Mon 22 Apr 2019 | 0-0 v Newport CountyMacclesfield Town 0-0 Newport County | Sky Bet League Two |
| 16 | Sat 27 Apr 2019 | 1-0 v Port ValePort Vale 0-1 Macclesfield Town | Sky Bet League Two |
| 17 | Sat 4 May 2019 | 1-1 v Cambridge UnitedMacclesfield Town 1-1 Cambridge United | Sky Bet League Two |
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