| 2023-04-10 | Dag and RedvChesterfieldNational League · England | 0–1 | National League · England |
| 2023-04-07 | ChesterfieldvYorkNational League · England | 1–3 | National League · England |
| 2023-04-01 | MaidenheadvChesterfieldNational League · England | 0–0 | National League · England |
| 2023-03-25 | ChesterfieldvHalifaxNational League · England | 2–0 | National League · England |
| 2023-03-18 | WokingvChesterfieldNational League · England | 0–1 | National League · England |
| 2023-03-14 | WealdstonevChesterfieldNational League · England | 0–4 | National League · England |
| 2023-03-11 | ChesterfieldvYeovilNational League · England | 1–1 | National League · England |
| 2023-03-07 | SouthendvChesterfieldNational League · England | 1–2 | National League · England |
| 2023-03-04 | GatesheadvChesterfieldNational League · England | 1–2 | National League · England |
| 2023-02-28 | WrexhamvChesterfieldNational League · England | 2–1 | National League · England |
| 2023-02-25 | ChesterfieldvOldhamNational League · England | 0–1 | National League · England |
| 2023-02-21 | ChesterfieldvWealdstoneNational League · England | 1–1 | National League · England |
| 2023-02-18 | SolihullvChesterfieldNational League · England | 0–0 | National League · England |
| 2023-02-14 | AldershotvChesterfieldNational League · England | 1–1 | National League · England |
| 2023-02-11 | ChesterfieldvNotts CountyNational League · England | 1–2 | National League · England |
| 2023-02-07 | ChesterfieldvWokingNational League · England | 1–3 | National League · England |
| 2023-02-04 | Boreham WoodvChesterfieldNational League · England | 1–0 | National League · England |
| 2023-01-28 | BarnetvChesterfieldNational League · England | 3–0 | National League · England |
| 2023-01-24 | ChesterfieldvAltrinchamNational League · England | 1–0 | National League · England |
| 2023-01-01 | ChesterfieldvScunthorpeNational League · England | 4–1 | National League · England |
| 2022-12-26 | ScunthorpevChesterfieldNational League · England | 1–2 | National League · England |
| 2022-12-10 | ChesterfieldvDorkingNational League · England | 3–1 | National League · England |
| 2022-12-03 | HalifaxvChesterfieldNational League · England | 1–0 | National League · England |
| 2022-11-19 | ChesterfieldvSolihullNational League · England | 2–0 | National League · England |
| 2022-11-12 | TorquayvChesterfieldNational League · England | 1–5 | National League · England |
| 2022-11-01 | ChesterfieldvGatesheadNational League · England | 2–1 | National League · England |
| 2022-10-29 | ChesterfieldvBoreham WoodNational League · England | 2–0 | National League · England |
| 2022-10-25 | YorkvChesterfieldNational League · England | 1–1 | National League · England |
| 2022-10-22 | ChesterfieldvBromleyNational League · England | 3–2 | National League · England |
| 2022-10-08 | EastleighvChesterfieldNational League · England | 2–1 | National League · England |
| 2022-10-04 | ChesterfieldvDag and RedNational League · England | 2–3 | National League · England |
| 2022-10-01 | ChesterfieldvMaidenheadNational League · England | 1–2 | National League · England |
| 2022-09-24 | MaidstonevChesterfieldNational League · England | 1–2 | National League · England |
| 2022-09-17 | YeovilvChesterfieldNational League · England | 2–2 | National League · England |
| 2022-09-13 | ChesterfieldvSouthendNational League · England | 3–2 | National League · England |
| 2022-09-03 | OldhamvChesterfieldNational League · England | 0–2 | National League · England |
| 2022-08-29 | AltrinchamvChesterfieldNational League · England | 1–2 | National League · England |
| 2022-08-26 | ChesterfieldvBarnetNational League · England | 3–1 | National League · England |
| 2022-08-20 | Notts CountyvChesterfieldNational League · England | 2–2 | National League · England |
| 2022-08-16 | ChesterfieldvWrexhamNational League · England | 2–0 | National League · England |
| 2022-08-13 | ChesterfieldvAldershotNational League · England | 1–0 | National League · England |
| 2022-08-06 | DorkingvChesterfieldNational League · England | 2–2 | National League · England |
| 2022-05-15 | ChesterfieldvWokingNational League · England | 0–0 | National League · England |
| 2022-05-07 | TorquayvChesterfieldNational League · England | 2–0 | National League · England |
| 2022-05-02 | ChesterfieldvStockportNational League · England | 0–1 | National League · England |
| 2022-04-30 | BromleyvChesterfieldNational League · England | 4–2 | National League · England |
| 2022-04-23 | ChesterfieldvDover AthleticNational League · England | 3–2 | National League · England |
| 2022-04-18 | HalifaxvChesterfieldNational League · England | 2–0 | National League · England |
| 2022-04-09 | WealdstonevChesterfieldNational League · England | 1–2 | National League · England |
| 2022-04-02 | ChesterfieldvGrimsbyNational League · England | 1–4 | National League · England |