| 2021-05-08 | SouthendvNewport CountyLeague Two · England | 1–1 | League Two · England |
| 2021-05-01 | BarrowvSouthendLeague Two · England | 1–2 | League Two · England |
| 2021-04-24 | SouthendvLeyton OrientLeague Two · England | 2–1 | League Two · England |
| 2021-04-20 | ColchestervSouthendLeague Two · England | 2–0 | League Two · England |
| 2021-04-17 | ExetervSouthendLeague Two · England | 0–0 | League Two · England |
| 2021-04-10 | SouthendvCrawley TownLeague Two · England | 0–0 | League Two · England |
| 2021-04-06 | MorecambevSouthendLeague Two · England | 1–1 | League Two · England |
| 2021-04-03 | SouthendvCarlisleLeague Two · England | 0–2 | League Two · England |
| 2021-03-27 | HarrogatevSouthendLeague Two · England | 0–1 | League Two · England |
| 2021-03-23 | SouthendvWalsallLeague Two · England | 0–0 | League Two · England |
| 2021-03-20 | ScunthorpevSouthendLeague Two · England | 1–1 | League Two · England |
| 2021-03-13 | SouthendvStevenageLeague Two · England | 0–0 | League Two · England |
| 2021-03-09 | SouthendvTranmereLeague Two · England | 0–2 | League Two · England |
| 2021-03-06 | OldhamvSouthendLeague Two · England | 0–0 | League Two · England |
| 2021-03-02 | CheltenhamvSouthendLeague Two · England | 1–0 | League Two · England |
| 2021-02-27 | SouthendvSalfordLeague Two · England | 0–0 | League Two · England |
| 2021-02-24 | Forest GreenvSouthendLeague Two · England | 1–3 | League Two · England |
| 2021-02-20 | SouthendvBoltonLeague Two · England | 0–1 | League Two · England |
| 2021-02-13 | CambridgevSouthendLeague Two · England | 0–0 | League Two · England |
| 2021-02-09 | Newport CountyvSouthendLeague Two · England | 0–1 | League Two · England |
| 2021-01-30 | Port ValevSouthendLeague Two · England | 5–1 | League Two · England |
| 2021-01-26 | SouthendvBradfordLeague Two · England | 1–3 | League Two · England |
| 2021-01-23 | SouthendvMansfieldLeague Two · England | 0–1 | League Two · England |
| 2021-01-19 | SouthendvCambridgeLeague Two · England | 1–2 | League Two · England |
| 2021-01-16 | GrimsbyvSouthendLeague Two · England | 0–0 | League Two · England |
| 2021-01-09 | SouthendvBarrowLeague Two · England | 1–0 | League Two · England |