| 2019-12-29 | PlymouthvStevenageLeague Two · England | 2–1 | League Two · England |
| 2019-12-26 | CheltenhamvPlymouthLeague Two · England | 0–1 | League Two · England |
| 2019-12-14 | PlymouthvMorecambeLeague Two · England | 3–0 | League Two · England |
| 2019-12-07 | CambridgevPlymouthLeague Two · England | 1–0 | League Two · England |
| 2019-11-23 | PlymouthvBradfordLeague Two · England | 2–1 | League Two · England |
| 2019-11-16 | Forest GreenvPlymouthLeague Two · England | 0–1 | League Two · England |
| 2019-10-26 | ExetervPlymouthLeague Two · England | 4–0 | League Two · England |
| 2019-10-22 | PlymouthvLeyton OrientLeague Two · England | 4–0 | League Two · England |
| 2019-10-19 | PlymouthvCarlisleLeague Two · England | 2–0 | League Two · England |
| 2019-10-12 | SwindonvPlymouthLeague Two · England | 1–1 | League Two · England |
| 2019-10-05 | PlymouthvScunthorpeLeague Two · England | 2–2 | League Two · England |
| 2019-09-28 | MansfieldvPlymouthLeague Two · England | 0–1 | League Two · England |
| 2019-09-21 | PlymouthvCheltenhamLeague Two · England | 0–2 | League Two · England |
| 2019-09-17 | Crawley TownvPlymouthLeague Two · England | 2–2 | League Two · England |
| 2019-09-14 | Port ValevPlymouthLeague Two · England | 1–0 | League Two · England |
| 2019-09-07 | PlymouthvOldhamLeague Two · England | 2–2 | League Two · England |
| 2019-08-31 | NorthamptonvPlymouthLeague Two · England | 3–1 | League Two · England |
| 2019-08-24 | PlymouthvWalsallLeague Two · England | 3–0 | League Two · England |
| 2019-08-20 | PlymouthvSalfordLeague Two · England | 2–2 | League Two · England |
| 2019-08-17 | Newport CountyvPlymouthLeague Two · England | 1–0 | League Two · England |
| 2019-08-10 | PlymouthvColchesterLeague Two · England | 1–0 | League Two · England |
| 2019-08-03 | CrewevPlymouthLeague Two · England | 0–3 | League Two · England |
| 2019-05-04 | PlymouthvScunthorpeLeague One · England | 3–2 | League One · England |
| 2019-04-27 | AccringtonvPlymouthLeague One · England | 5–1 | League One · England |
| 2019-04-22 | PlymouthvBarnsleyLeague One · England | 0–3 | League One · England |
| 2019-04-19 | GillinghamvPlymouthLeague One · England | 3–1 | League One · England |
| 2019-04-13 | DoncastervPlymouthLeague One · England | 2–0 | League One · England |
| 2019-04-06 | PlymouthvCharltonLeague One · England | 0–2 | League One · England |
| 2019-03-30 | BlackpoolvPlymouthLeague One · England | 2–2 | League One · England |
| 2019-03-23 | PlymouthvBristol RvsLeague One · England | 2–2 | League One · England |
| 2019-03-16 | Fleetwood TownvPlymouthLeague One · England | 2–0 | League One · England |
| 2019-03-12 | PlymouthvShrewsburyLeague One · England | 2–1 | League One · England |
| 2019-03-09 | PlymouthvLutonLeague One · England | 0–0 | League One · England |
| 2019-03-02 | SunderlandvPlymouthLeague One · England | 2–0 | League One · England |
| 2019-02-23 | PlymouthvRochdaleLeague One · England | 5–1 | League One · England |
| 2019-02-16 | BradfordvPlymouthLeague One · England | 0–0 | League One · England |
| 2019-02-09 | PlymouthvPortsmouthLeague One · England | 1–1 | League One · England |
| 2019-02-02 | PeterborovPlymouthLeague One · England | 0–1 | League One · England |
| 2019-01-26 | WycombevPlymouthLeague One · England | 1–0 | League One · England |
| 2019-01-22 | PlymouthvWalsallLeague One · England | 2–1 | League One · England |
| 2019-01-19 | PlymouthvCoventryLeague One · England | 2–1 | League One · England |
| 2019-01-12 | SouthendvPlymouthLeague One · England | 2–3 | League One · England |
| 2019-01-01 | PlymouthvOxfordLeague One · England | 3–0 | League One · England |