| 2023-12-26 | SolihullvChesterfieldNational League · England | 2–0 | National League · England |
| 2023-12-23 | ChesterfieldvAldershotNational League · England | 4–1 | National League · England |
| 2023-12-16 | HartlepoolvChesterfieldNational League · England | 0–1 | National League · England |
| 2023-11-25 | ChesterfieldvEastleighNational League · England | 3–2 | National League · England |
| 2023-11-21 | WokingvChesterfieldNational League · England | 0–2 | National League · England |
| 2023-11-18 | SouthendvChesterfieldNational League · England | 2–1 | National League · England |
| 2023-11-11 | ChesterfieldvBarnetNational League · England | 4–2 | National League · England |
| 2023-10-28 | KidderminstervChesterfieldNational League · England | 1–3 | National League · England |
| 2023-10-24 | ChesterfieldvYorkNational League · England | 4–0 | National League · England |
| 2023-10-07 | Boreham WoodvChesterfieldNational League · England | 0–2 | National League · England |
| 2023-10-03 | ChesterfieldvBromleyNational League · England | 2–0 | National League · England |
| 2023-09-30 | MaidenheadvChesterfieldNational League · England | 1–1 | National League · England |
| 2023-09-26 | RochdalevChesterfieldNational League · England | 1–2 | National League · England |
| 2023-09-23 | ChesterfieldvWealdstoneNational League · England | 3–2 | National League · England |
| 2023-09-19 | ChesterfieldvHalifaxNational League · England | 3–2 | National League · England |
| 2023-09-16 | EbbsfleetvChesterfieldNational League · England | 0–1 | National League · England |
| 2023-09-09 | ChesterfieldvDag and RedNational League · England | 3–1 | National League · England |
| 2023-09-02 | AldershotvChesterfieldNational League · England | 3–4 | National League · England |
| 2023-08-28 | ChesterfieldvHartlepoolNational League · England | 3–2 | National League · England |
| 2023-08-26 | AltrinchamvChesterfieldNational League · England | 2–1 | National League · England |
| 2023-08-19 | ChesterfieldvOldhamNational League · England | 1–1 | National League · England |
| 2023-08-15 | Oxford CityvChesterfieldNational League · England | 1–2 | National League · England |
| 2023-08-12 | FyldevChesterfieldNational League · England | 2–4 | National League · England |
| 2023-08-05 | ChesterfieldvDorkingNational League · England | 4–3 | National League · England |
| 2023-04-29 | ChesterfieldvMaidstoneNational League · England | 4–0 | National League · England |
| 2023-04-22 | BromleyvChesterfieldNational League · England | 2–0 | National League · England |
| 2023-04-18 | ChesterfieldvTorquayNational League · England | 5–1 | National League · England |
| 2023-04-15 | ChesterfieldvEastleighNational League · England | 3–2 | National League · England |
| 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 |