| 1 | Sat 24 Aug 2019 | 157-2 v Bridon RopesBridon Ropes 2-7 Chichester City | Emirates FA Cup Preliminary Round |
| 2 | Mon 26 Aug 2019 | 152-1 v Burgess Hill TownBurgess Hill Town 1-2 Chichester City | BetVictor Isthmian South East Division |
| 3 | Tue 3 Sep 2019 | 10 0-2 v Hastings UnitedChichester City 0-2 Hastings United | Velocity Trophy Group 4 |
| 4 | Sat 7 Sep 2019 | 122-0 v Chalfont St PeterChichester City 2-0 Chalfont St Peter | Emirates FA Cup First Qualifying Round |
| 5 | Sat 28 Sep 2019 | 122-1 v Three BridgesChichester City 2-1 Three Bridges | Buildbase FA Trophy Extra Preliminary Round |
| 6 | Tue 8 Oct 2019 | 126-2 v Three BridgesThree Bridges 2-6 Chichester City | Velocity Trophy Group 4 |
| 7 | Sat 12 Oct 2019 | 142-4 v Barton RoversBarton Rovers 4-2 Chichester City | Buildbase FA Trophy Preliminary Round |
| 8 | Tue 22 Oct 2019 | 70-5 v East Grinstead TownChichester City 0-5 East Grinstead Town | Velocity Trophy Group 4 |
| 9 | Tue 19 Nov 2019 | 170-2 v Haywards Heath TownHaywards Heath Town 2-0 Chichester City | Velocity Trophy Group 4 |
| 10 | Sat 7 Dec 2019 | 141-5 v Hastings UnitedHastings United 5-1 Chichester City | BetVictor Isthmian South East Division |
| 11 | Tue 7 Jan 2020 | 163-0 v VCD AthleticVCD Athletic 0-3 Chichester City | BetVictor Isthmian South East Division |
| 12 | Tue 28 Jan 2020 | 40-3 v Burgess Hill TownBurgess Hill Town 3-0 Chichester City | Velocity Trophy Group 4 |
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