| 1 | Tue 4 Sep 2018 | 203-3 v BlackpoolMacclesfield Town 3-3 Blackpool | Checkatrade Trophy Northern Group C |
| 2 | Sat 8 Sep 2018 | 200-1 v StevenageStevenage 1-0 Macclesfield Town | Sky Bet League Two |
| 3 | Sat 15 Sep 2018 | 20 1-2 v Lincoln CityMacclesfield Town 1-2 Lincoln City | Sky Bet League Two |
| 4 | Sat 22 Sep 2018 | 201-2 v MorecambeMorecambe 2-1 Macclesfield Town | Sky Bet League Two |
| 5 | Sat 29 Sep 2018 | 201-1 v Forest Green RoversMacclesfield Town 1-1 Forest Green Rovers | Sky Bet League Two |
| 6 | Tue 2 Oct 2018 | 20 3-3 v Newport CountyNewport County 3-3 Macclesfield Town | Sky Bet League Two |
| 7 | Sat 6 Oct 2018 | 20 0-1 v Notts CountyMacclesfield Town 0-1 Notts County | Sky Bet League Two |
| 8 | Tue 9 Oct 2018 | 201-4 v Accrington StanleyAccrington Stanley 4-1 Macclesfield Town | Checkatrade Trophy Northern Group C |
| 9 | Fri 12 Oct 2018 | 200-1 v Tranmere RoversTranmere Rovers 1-0 Macclesfield Town | Sky Bet League Two |
| 10 | Sat 20 Oct 2018 | 202-1 v Carlisle UnitedMacclesfield Town 2-1 Carlisle United | Sky Bet League Two |
| 11 | Tue 23 Oct 2018 | 200-5 v Northampton TownMacclesfield Town 0-5 Northampton Town | Sky Bet League Two |
| 12 | Sat 27 Oct 2018 | 200-1 v Cambridge UnitedCambridge United 1-0 Macclesfield Town | Sky Bet League Two |
| 13 | Sat 3 Nov 2018 | 201-4 v BuryMacclesfield Town 1-4 Bury | Sky Bet League Two |
| 14 | Sat 10 Nov 2018 | 201-2 v Maidstone UnitedMaidstone United 2-1 Macclesfield Town | Emirates FA Cup First Round |
| 15 | Sat 24 Nov 2018 | 20 1-0 v Yeovil TownMacclesfield Town 1-0 Yeovil Town | Sky Bet League Two |
| 16 | Tue 27 Nov 2018 | 201-0 v Exeter CityExeter City 0-1 Macclesfield Town | Sky Bet League Two |
| 17 | Sat 8 Dec 2018 | 200-1 v Colchester UnitedColchester United 1-0 Macclesfield Town | Sky Bet League Two |
| 18 | Sat 5 Jan 2019 | 201-2 v Swindon TownMacclesfield Town 1-2 Swindon Town | Sky Bet League Two |
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