| 1 | Fri 12 Oct 2018 | 0-1 v Tranmere RoversTranmere Rovers 1-0 Macclesfield Town | Sky Bet League Two |
| 2 | Sat 20 Oct 2018 | 2-1 v Carlisle UnitedMacclesfield Town 2-1 Carlisle United | Sky Bet League Two |
| 3 | Tue 23 Oct 2018 | 0-5 v Northampton TownMacclesfield Town 0-5 Northampton Town | Sky Bet League Two |
| 4 | Sat 27 Oct 2018 | 0-1 v Cambridge UnitedCambridge United 1-0 Macclesfield Town | Sky Bet League Two |
| 5 | Sat 3 Nov 2018 | 1-4 v BuryMacclesfield Town 1-4 Bury | Sky Bet League Two |
| 6 | Sat 10 Nov 2018 | 1-2 v Maidstone UnitedMaidstone United 2-1 Macclesfield Town | Emirates FA Cup First Round |
| 7 | Sat 24 Nov 2018 | 1-0 v Yeovil TownMacclesfield Town 1-0 Yeovil Town | Sky Bet League Two |
| 8 | Sat 8 Dec 2018 | 0-1 v Colchester UnitedColchester United 1-0 Macclesfield Town | Sky Bet League Two |
| 9 | Sat 15 Dec 2018 | 2-0 v Crawley TownMacclesfield Town 2-0 Crawley Town | Sky Bet League Two |
| 10 | Sat 22 Dec 2018 | 0-0 v Port ValeMacclesfield Town 0-0 Port Vale | Sky Bet League Two |
| 11 | Wed 26 Dec 2018 | 2-1 v Notts CountyNotts County 1-2 Macclesfield Town | Sky Bet League Two |
| 12 | Sat 2 Mar 2019 | 0-3 v BuryBury 3-0 Macclesfield Town | Sky Bet League Two |
| 13 | Sat 9 Mar 2019 | 1-3 v Milton Keynes DonsMacclesfield Town 1-3 Milton Keynes Dons | Sky Bet League Two |
| 14 | Sat 16 Mar 2019 | 2-0 v Yeovil TownYeovil Town 0-2 Macclesfield Town | Sky Bet League Two |
| 15 | Sat 23 Mar 2019 | 2-2 v StevenageMacclesfield Town 2-2 Stevenage | Sky Bet League Two |
| 16 | Sat 30 Mar 2019 | 1-1 v Lincoln CityLincoln City 1-1 Macclesfield Town | Sky Bet League Two |
| 17 | Sat 6 Apr 2019 | 1-1 v MorecambeMacclesfield Town 1-1 Morecambe | Sky Bet League Two |
| 18 | Tue 9 Apr 2019 | 3-2 v Exeter CityMacclesfield Town 3-2 Exeter City | Sky Bet League Two |
| 19 | Sat 13 Apr 2019 | 0-2 v Forest Green RoversForest Green Rovers 2-0 Macclesfield Town | Sky Bet League Two |
| 20 | Fri 19 Apr 2019 | 1-3 v Northampton TownNorthampton Town 3-1 Macclesfield Town | Sky Bet League Two |
| 21 | Sat 27 Apr 2019 | 1-0 v Port ValePort Vale 0-1 Macclesfield Town | Sky Bet League Two |
| 22 | Sat 4 May 2019 | 1-1 v Cambridge UnitedMacclesfield Town 1-1 Cambridge United | Sky Bet League Two |
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