| 2022-03-26 | Notts CountyvChesterfieldNational League · England | 1–1 | National League · England |
| 2022-03-22 | AltrinchamvChesterfieldNational League · England | 1–0 | National League · England |
| 2022-03-19 | ChesterfieldvMaidenheadNational League · England | 1–0 | National League · England |
| 2022-03-12 | Boreham WoodvChesterfieldNational League · England | 1–1 | National League · England |
| 2022-03-05 | ChesterfieldvSouthendNational League · England | 2–2 | National League · England |
| 2022-03-01 | ChesterfieldvNotts CountyNational League · England | 3–1 | National League · England |
| 2022-02-26 | ChesterfieldvYeovilNational League · England | 1–0 | National League · England |
| 2022-02-22 | ChesterfieldvWrexhamNational League · England | 0–2 | National League · England |
| 2022-02-19 | ChesterfieldvSolihullNational League · England | 2–3 | National League · England |
| 2022-02-12 | WeymouthvChesterfieldNational League · England | 1–1 | National League · England |
| 2022-02-08 | StockportvChesterfieldNational League · England | 2–2 | National League · England |
| 2022-02-05 | ChesterfieldvDag and RedNational League · England | 2–1 | National League · England |
| 2022-01-29 | EastleighvChesterfieldNational League · England | 0–1 | National League · England |
| 2022-01-22 | ChesterfieldvAldershotNational League · England | 0–0 | National League · England |
| 2022-01-18 | MaidenheadvChesterfieldNational League · England | 3–2 | National League · England |
| 2022-01-15 | BarnetvChesterfieldNational League · England | 1–4 | National League · England |
| 2022-01-01 | ChesterfieldvKings LynnNational League · England | 1–0 | National League · England |
| 2021-12-28 | ChesterfieldvHalifaxNational League · England | 1–1 | National League · England |
| 2021-12-11 | GrimsbyvChesterfieldNational League · England | 0–1 | National League · England |
| 2021-11-23 | ChesterfieldvAltrinchamNational League · England | 2–2 | National League · England |
| 2021-11-20 | SolihullvChesterfieldNational League · England | 0–2 | National League · England |
| 2021-11-13 | ChesterfieldvWeymouthNational League · England | 4–0 | National League · England |
| 2021-10-30 | Dag and RedvChesterfieldNational League · England | 2–2 | National League · England |
| 2021-10-26 | ChesterfieldvEastleighNational League · England | 1–0 | National League · England |
| 2021-10-23 | ChesterfieldvBoreham WoodNational League · England | 2–1 | National League · England |
| 2021-10-09 | SouthendvChesterfieldNational League · England | 0–4 | National League · England |
| 2021-10-05 | WrexhamvChesterfieldNational League · England | 1–1 | National League · England |
| 2021-09-28 | WokingvChesterfieldNational League · England | 3–1 | National League · England |
| 2021-09-25 | ChesterfieldvTorquayNational League · England | 2–2 | National League · England |
| 2021-09-18 | YeovilvChesterfieldNational League · England | 0–2 | National League · England |
| 2021-09-14 | ChesterfieldvBarnetNational League · England | 4–2 | National League · England |
| 2021-09-11 | Dover AthleticvChesterfieldNational League · England | 0–0 | National League · England |
| 2021-09-04 | ChesterfieldvBromleyNational League · England | 2–2 | National League · England |
| 2021-08-30 | Kings LynnvChesterfieldNational League · England | 0–2 | National League · England |
| 2021-08-28 | ChesterfieldvWealdstoneNational League · England | 2–0 | National League · England |
| 2021-08-21 | AldershotvChesterfieldNational League · England | 0–2 | National League · England |
| 2021-05-29 | HalifaxvChesterfieldNational League · England | 1–2 | National League · England |
| 2021-05-22 | ChesterfieldvDag and RedNational League · England | 2–1 | National League · England |
| 2021-05-15 | ChesterfieldvWealdstoneNational League · England | 0–0 | National League · England |
| 2021-05-11 | ChesterfieldvKings LynnNational League · England | 4–1 | National League · England |
| 2021-05-08 | WokingvChesterfieldNational League · England | 1–4 | National League · England |
| 2021-05-03 | ChesterfieldvTorquayNational League · England | 0–2 | National League · England |
| 2021-05-01 | HartlepoolvChesterfieldNational League · England | 3–1 | National League · England |
| 2021-04-27 | BromleyvChesterfieldNational League · England | 1–2 | National League · England |
| 2021-04-24 | WrexhamvChesterfieldNational League · England | 0–0 | National League · England |
| 2021-04-20 | ChesterfieldvHalifaxNational League · England | 1–2 | National League · England |
| 2021-04-17 | ChesterfieldvBromleyNational League · England | 1–2 | National League · England |
| 2021-04-13 | ChesterfieldvBoreham WoodNational League · England | 0–0 | National League · England |
| 2021-04-10 | Kings LynnvChesterfieldNational League · England | 1–2 | National League · England |
| 2021-04-02 | EastleighvChesterfieldNational League · England | 0–1 | National League · England |