| 1 | Tue 13 Aug 2019 | 2-1 v StevenageStevenage 1-2 Southend United | Carabao Cup First Round |
| 2 | Tue 20 Aug 2019 | 0-2 v Peterborough UnitedSouthend United 0-2 Peterborough United | Sky Bet League One |
| 3 | Sat 24 Aug 2019 | 3-4 v Wycombe WanderersWycombe Wanderers 4-3 Southend United | Sky Bet League One |
| 4 | Tue 27 Aug 2019 | 1-4 v Milton Keynes DonsSouthend United 1-4 Milton Keynes Dons | Carabao Cup Second Round |
| 5 | Tue 3 Sep 2019 | 0-2 v Leyton OrientLeyton Orient 2-0 Southend United | Leasing.com Trophy Southern Group C |
| 6 | Sat 14 Sep 2019 | 3-3 v Fleetwood TownSouthend United 3-3 Fleetwood Town | Sky Bet League One |
| 7 | Sat 26 Oct 2019 | 3-2 v Sutton UnitedSutton United 2-3 Ebbsfleet United | Vanarama National League |
| 8 | Tue 29 Oct 2019 | 4-0 v ChorleyChorley 0-4 Ebbsfleet United | Vanarama National League |
| 9 | Sat 2 Nov 2019 | 2-2 v ChesterfieldEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 10 | Sat 9 Nov 2019 | 2-3 v Notts CountyEbbsfleet United 2-3 Notts County | Emirates FA Cup First Round |
| 11 | Tue 26 Nov 2019 | 2-5 v BarnetBarnet 5-2 Ebbsfleet United | Vanarama National League |
| 12 | Sat 30 Nov 2019 | 2-1 v WrexhamEbbsfleet United 2-1 Wrexham | Vanarama National League |
| 13 | Sat 28 Dec 2019 | 0-1 v Dover AthleticEbbsfleet United 0-1 Dover Athletic | Vanarama National League |
| 14 | Wed 1 Jan 2020 | 1-1 v Dagenham & RedbridgeEbbsfleet United 1-1 Dagenham & Redbridge | Vanarama National League |
| 15 | Sat 15 Feb 2020 | 1-0 v ChorleyEbbsfleet United 1-0 Chorley | Vanarama National League |
| 16 | Sat 22 Feb 2020 | 0-4 v ChesterfieldChesterfield 4-0 Ebbsfleet United | Vanarama National League |
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