| 1 | Sat 8 Jul 2023 | 140-1 v Weston-super-MareDorchester Town 0-1 Weston-super-Mare | Friendly |
| 2 | Tue 11 Jul 2023 | 82-0 v Portland UnitedPortland United 0-2 Dorchester Town | Friendly |
| 3 | Sat 15 Jul 2023 | 111-1 v Frome TownDorchester Town 1-1 Frome Town | Friendly |
| 4 | Tue 18 Jul 2023 | 120-5 v Yeovil TownDorchester Town 0-5 Yeovil Town | Friendly |
| 5 | Sat 22 Jul 2023 | 81-2 v Wimborne TownDorchester Town 1-2 Wimborne Town | Friendly |
| 6 | Tue 25 Jul 2023 | 83-0 v EastleighDorchester Town 3-0 Eastleigh | Friendly |
| 7 | Sat 5 Aug 2023 | 82-3 v Merthyr TownMerthyr Town 3-2 Dorchester Town | Southern League - Premier South |
| 8 | Sat 12 Aug 2023 | 22-2 v Harrow BoroughDorchester Town 2-2 Harrow Borough | Southern League - Premier South |
| 9 | Tue 15 Aug 2023 | 110-4 v Winchester CityDorchester Town 0-4 Winchester City | Southern League - Premier South |
| 10 | Sat 19 Aug 2023 | 123-6 v Walton & HershamWalton & Hersham 6-3 Dorchester Town | Southern League - Premier South |
| 11 | Sat 26 Aug 2023 | 110-2 v Chesham UnitedDorchester Town 0-2 Chesham United | Southern League - Premier South |
| 12 | Mon 28 Aug 2023 | 112-1 v Poole TownPoole Town 1-2 Dorchester Town | Southern League - Premier South |
| 13 | Sat 2 Sep 2023 | 40-2 v Plymouth ParkwayPlymouth Parkway 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 14 | Sat 9 Sep 2023 | 82-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 15 | Tue 12 Sep 2023 | 151-1 v Hungerford TownHungerford Town 1-1 Dorchester Town | Southern League - Premier South |
| 16 | Sat 23 Sep 2023 | 163-1 v Didcot TownDorchester Town 3-1 Didcot Town | Southern League - Premier South |
| 17 | Tue 26 Sep 2023 | 70-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 18 | Wed 11 Oct 2023 | 112-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 19 | Sat 21 Oct 2023 | 140-1 v HendonHendon 1-0 Dorchester Town | Southern League - Premier South |
| 20 | Tue 24 Oct 2023 | 71-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 21 | Sat 11 Nov 2023 | 144-1 v Basingstoke TownDorchester Town 4-1 Basingstoke Town | Southern League - Premier South |
| 22 | Tue 14 Nov 2023 | 141-2 v Bracknell TownDorchester Town 1-2 Bracknell Town | Southern League - Premier South |
| 23 | Sat 25 Nov 2023 | 162-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 24 | Sat 9 Dec 2023 | 122-1 v Swindon SupermarineSwindon Supermarine 1-2 Dorchester Town | Southern League - Premier South |
| 25 | Sat 16 Dec 2023 | 71-2 v Walton & HershamDorchester Town 1-2 Walton & Hersham | Southern League - Premier South |
| 26 | Sat 23 Dec 2023 | 40-2 v Chesham UnitedChesham United 2-0 Dorchester Town | Southern League - Premier South |
| 27 | Tue 26 Dec 2023 | 71-2 v Poole TownDorchester Town 1-2 Poole Town | Southern League - Premier South |
| 28 | Sat 6 Jan 2024 | 122-4 v Hungerford TownDorchester Town 2-4 Hungerford Town | Southern League - Premier South |
| 29 | Sat 13 Jan 2024 | 152-0 v Harrow BoroughHarrow Borough 0-2 Dorchester Town | Southern League - Premier South |
| 30 | Sat 20 Jan 2024 | 153-2 v Merthyr TownDorchester Town 3-2 Merthyr Town | Southern League - Premier South |
| 31 | Sat 10 Feb 2024 | 120-3 v Gosport BoroughDorchester Town 0-3 Gosport Borough | Southern League - Premier South |
| 32 | Sat 17 Feb 2024 | 143-1 v Bracknell TownBracknell Town 1-3 Dorchester Town | Southern League - Premier South |
| 33 | Sat 23 Mar 2024 | 141-0 v SalisburyDorchester Town 1-0 Salisbury | Southern League - Premier South |
| 34 | Sat 6 Apr 2024 | 141-0 v Hayes & Yeading UnitedHayes & Yeading United 0-1 Dorchester Town | Southern League - Premier South |
| 35 | Tue 9 Apr 2024 | 172-1 v SholingSholing 1-2 Dorchester Town | Southern League - Premier South |
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