| 1 | Tue 4 Jul 2023 | 13-1 v Horbury TownHorbury Town 1-3 Ossett United | Friendly |
| 2 | Fri 7 Jul 2023 | 13-2 v Armthorpe WelfareArmthorpe Welfare 2-3 Ossett United | Friendly |
| 3 | Fri 14 Jul 2023 | 11-0 v Tadcaster AlbionTadcaster Albion 0-1 Ossett United | Friendly |
| 4 | Tue 18 Jul 2023 | 12-0 v Hemsworth Miners WelfareHemsworth Miners Welfare 0-2 Ossett United | Friendly |
| 5 | Sat 22 Jul 2023 | 11-4 v Goole AFCGoole AFC 4-1 Ossett United | Friendly |
| 6 | Tue 25 Jul 2023 | 10-3 v Garforth TownGarforth Town 3-0 Ossett United | Friendly |
| 7 | Sat 29 Jul 2023 | 11-0 v WidnesOssett United 1-0 Widnes | Friendly |
| 8 | Sat 12 Aug 2023 | 11-3 v SheffieldSheffield 3-1 Ossett United | Northern Premier League - East Division |
| 9 | Tue 15 Aug 2023 | 12-4 v DunstonOssett United 2-4 Dunston | Northern Premier League - East Division |
| 10 | Sat 19 Aug 2023 | 12-0 v WythenshaweOssett United 2-0 Wythenshawe | Emirates FA Cup Preliminary Round |
| 11 | Tue 22 Aug 2023 | 1 1-0 v Ashington AFCAshington AFC 0-1 Ossett United | Northern Premier League - East Division |
| 12 | Sat 26 Aug 2023 | 10-1 v Stockton TownOssett United 0-1 Stockton Town | Northern Premier League - East Division |
| 13 | Mon 28 Aug 2023 | 10-4 v Pontefract CollieriesPontefract Collieries 4-0 Ossett United | Northern Premier League - East Division |
| 14 | Sat 2 Sep 2023 | 10-3 v Marske UnitedOssett United 0-3 Marske United | Emirates FA Cup First Qualifying Round |
| 15 | Sat 9 Sep 2023 | 11-2 v North FerribyNorth Ferriby 2-1 Ossett United | Isuzu FA Trophy First Qualifying Round |
| 16 | Sat 16 Sep 2023 | 13-1 v Newton AycliffeNewton Aycliffe 1-3 Ossett United | Northern Premier League - East Division |
| 17 | Sat 30 Sep 2023 | 10-2 v Grimsby BoroughOssett United 0-2 Grimsby Borough | Northern Premier League - East Division |
| 18 | Sat 7 Oct 2023 | 12-1 v Consett AFCConsett AFC 1-2 Ossett United | Northern Premier League - East Division |
| 19 | Tue 10 Oct 2023 | 12-0 v Horbury TownOssett United 2-0 Horbury Town | The West Riding County Cup First Round |
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