| 1 | Sat 7 Jul 2018 | 42-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Portsmouth | Friendly |
| 2 | Sat 11 Aug 2018 | 42-1 v BlackpoolBlackpool 1-2 Portsmouth | Sky Bet League One |
| 3 | Tue 4 Sep 2018 | 44-0 v GillinghamPortsmouth 4-0 Gillingham | Checkatrade Trophy Southern Group A |
| 4 | Tue 9 Oct 2018 | 41-0 v Crawley TownCrawley Town 0-1 Portsmouth | Checkatrade Trophy Southern Group A |
| 5 | Sat 19 Jan 2019 | 2-1 v Tranmere RoversTranmere Rovers 1-2 Swindon Town | Sky Bet League Two |
| 6 | Sat 26 Jan 2019 | 0-1 v Crawley TownSwindon Town 0-1 Crawley Town | Sky Bet League Two |
| 7 | Sat 9 Feb 2019 | 3-2 v Milton Keynes DonsMilton Keynes Dons 2-3 Swindon Town | Sky Bet League Two |
| 8 | Tue 12 Feb 2019 | 2-0 v Forest Green RoversSwindon Town 2-0 Forest Green Rovers | Sky Bet League Two |
| 9 | Sat 16 Mar 2019 | 0-0 v Port ValeSwindon Town 0-0 Port Vale | Sky Bet League Two |
| 10 | Sat 23 Mar 2019 | 4-0 v MorecambeSwindon Town 4-0 Morecambe | Sky Bet League Two |
| 11 | Sat 30 Mar 2019 | 3-1 v BuryBury 1-3 Swindon Town | Sky Bet League Two |
| 12 | Sat 6 Apr 2019 | 1-1 v Yeovil TownSwindon Town 1-1 Yeovil Town | Sky Bet League Two |
| 13 | Tue 9 Apr 2019 | 0-0 v Newport CountyNewport County 0-0 Swindon Town | Sky Bet League Two |
| 14 | Sat 13 Apr 2019 | 2-2 v Oldham AthleticOldham Athletic 2-2 Swindon Town | Sky Bet League Two |
| 15 | Fri 19 Apr 2019 | 0-0 v Cambridge UnitedCambridge United 0-0 Swindon Town | Sky Bet League Two |
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