| 1 | Sat 22 Jul 2023 | 111-2 v Wimborne TownDorchester Town 1-2 Wimborne Town | Friendly |
| 2 | Tue 25 Jul 2023 | 113-0 v EastleighDorchester Town 3-0 Eastleigh | Friendly |
| 3 | Sat 5 Aug 2023 | 112-3 v Merthyr TownMerthyr Town 3-2 Dorchester Town | Southern League - Premier South |
| 4 | Mon 28 Aug 2023 | 122-1 v Poole TownPoole Town 1-2 Dorchester Town | Southern League - Premier South |
| 5 | Sat 2 Sep 2023 | 30-2 v Plymouth ParkwayPlymouth Parkway 2-0 Dorchester Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 9 Sep 2023 | 32-1 v Swindon SupermarineDorchester Town 2-1 Swindon Supermarine | Southern League - Premier South |
| 7 | Sat 23 Sep 2023 | 33-1 v Didcot TownDorchester Town 3-1 Didcot Town | Southern League - Premier South |
| 8 | Tue 26 Sep 2023 | 30-5 v Plymouth ParkwayPlymouth Parkway 5-0 Dorchester Town | Southern League - Premier South |
| 9 | Sat 7 Oct 2023 | 31-3 v Merthyr TownMerthyr Town 3-1 Dorchester Town | Isuzu FA Trophy Third Qualifying Round |
| 10 | Wed 11 Oct 2023 | 32-2 v Gosport BoroughGosport Borough 2-2 Dorchester Town | Southern League - Premier South |
| 11 | Sat 21 Oct 2023 | 30-1 v HendonHendon 1-0 Dorchester Town | Southern League - Premier South |
| 12 | Tue 24 Oct 2023 | 31-2 v SholingDorchester Town 1-2 Sholing | Southern League - Premier South |
| 13 | Sat 28 Oct 2023 | 31-1 v Hayes & Yeading UnitedDorchester Town 1-1 Hayes & Yeading United | Southern League - Premier South |
| 14 | Sat 11 Nov 2023 | 34-1 v Basingstoke TownDorchester Town 4-1 Basingstoke Town | Southern League - Premier South |
| 15 | Tue 14 Nov 2023 | 31-2 v Bracknell TownDorchester Town 1-2 Bracknell Town | Southern League - Premier South |
| 16 | Sat 25 Nov 2023 | 32-3 v SalisburySalisbury 3-2 Dorchester Town | Southern League - Premier South |
| 17 | Sat 9 Dec 2023 | 32-1 v Swindon SupermarineSwindon Supermarine 1-2 Dorchester Town | Southern League - Premier South |
| 18 | Sat 16 Dec 2023 | 31-2 v Walton & HershamDorchester Town 1-2 Walton & Hersham | Southern League - Premier South |
| 19 | Sat 23 Dec 2023 | 30-2 v Chesham UnitedChesham United 2-0 Dorchester Town | Southern League - Premier South |
| 20 | Tue 26 Dec 2023 | 31-2 v Poole TownDorchester Town 1-2 Poole Town | Southern League - Premier South |
| 21 | Sat 6 Jan 2024 | 32-4 v Hungerford TownDorchester Town 2-4 Hungerford Town | Southern League - Premier South |
| 22 | Sat 13 Jan 2024 | 32-0 v Harrow BoroughHarrow Borough 0-2 Dorchester Town | Southern League - Premier South |
| 23 | Sat 20 Jan 2024 | 33-2 v Merthyr TownDorchester Town 3-2 Merthyr Town | Southern League - Premier South |
| 24 | Sat 27 Jan 2024 | 30-0 v Plymouth ParkwayDorchester Town 0-0 Plymouth Parkway | Southern League - Premier South |
| 25 | Sat 3 Feb 2024 | 31-0 v Didcot TownDidcot Town 0-1 Dorchester Town | Southern League - Premier South |
| 26 | Tue 6 Feb 2024 | 31-1 v Hanwell TownHanwell Town 1-1 Dorchester Town | Southern League - Premier South |
| 27 | Sat 10 Feb 2024 | 30-3 v Gosport BoroughDorchester Town 0-3 Gosport Borough | Southern League - Premier South |
| 28 | Sat 17 Feb 2024 | 33-1 v Bracknell TownBracknell Town 1-3 Dorchester Town | Southern League - Premier South |
| 29 | Sat 24 Feb 2024 | 32-2 v HendonDorchester Town 2-2 Hendon | Southern League - Premier South |
| 30 | Wed 28 Feb 2024 | 34-4 v AFC TottonAFC Totton 4-4 Dorchester Town | Southern League - Premier South |
| 31 | Sat 9 Mar 2024 | 32-1 v Beaconsfield TownDorchester Town 2-1 Beaconsfield Town | Southern League - Premier South |
| 32 | Sat 16 Mar 2024 | 34-3 v Beaconsfield TownBeaconsfield Town 3-4 Dorchester Town | Southern League - Premier South |
| 33 | Sat 23 Mar 2024 | 31-0 v SalisburyDorchester Town 1-0 Salisbury | Southern League - Premier South |
| 34 | Sat 30 Mar 2024 | 31-1 v Winchester CityWinchester City 1-1 Dorchester Town | Southern League - Premier South |
| 35 | Mon 1 Apr 2024 | 32-1 v Tiverton TownDorchester Town 2-1 Tiverton Town | Southern League - Premier South |
| 36 | Sat 6 Apr 2024 | 31-0 v Hayes & Yeading UnitedHayes & Yeading United 0-1 Dorchester Town | Southern League - Premier South |
| 37 | Tue 9 Apr 2024 | 32-1 v SholingSholing 1-2 Dorchester Town | Southern League - Premier South |
| 38 | Sat 13 Apr 2024 | 32-1 v Hanwell TownDorchester Town 2-1 Hanwell Town | Southern League - Premier South |
| 39 | Tue 16 Apr 2024 | 32-0 v Tiverton TownTiverton Town 0-2 Dorchester Town | Southern League - Premier South |
| 40 | Sat 20 Apr 2024 | 31-3 v Basingstoke TownBasingstoke Town 3-1 Dorchester Town | Southern League - Premier South |
| 41 | Sat 27 Apr 2024 | 30-4 v AFC TottonDorchester Town 0-4 AFC Totton | Southern League - Premier South |
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