| 2019-08-03 15:00:593rd August 2019 |   Havant & Waterlooville vs Welling United | 1 - 1 | Vanarama National League South | The Westleigh | Report |
- |
| 2019-08-06 19:45:516th August 2019 |  Welling United vs Maidstone United | 1 - 0 | Vanarama National League South | Park View Road | Report |
1015 |
| 2019-08-10 15:00:3010th August 2019 |  Welling United vs Bath City | 0 - 3 | Vanarama National League South | Park View Road | Report |
416 |
| 2019-08-13 19:45:5213th August 2019 |  Billericay Town vs Welling United | 2 - 1 | Vanarama National League South | New Lodge | Report |
- |
| 2019-08-17 15:00:0817th August 2019 |  Welling United vs Oxford City | 3 - 1 | Vanarama National League South | Park View Road | Report |
424 |
| 2019-08-24 15:00:0824th August 2019 |  Chelmsford City vs Welling United | 1 - 1 | Vanarama National League South | Melbourne Community Stadium | Report |
747 |
| 2019-08-26 15:00:1326th August 2019 |  Welling United vs Tonbridge Angels | 4 - 2 | Vanarama National League South | Park View Road | Report |
669 |
| 2019-08-31 15:00:5231st August 2019 |  Concord Rangers vs Welling United | 3 - 0 | Vanarama National League South | The Aspect Arena | Report |
284 |
| 2019-09-03 19:45:403rd September 2019 |  Welling United vs Eastbourne | 0 - 0 | Vanarama National League South | Park View Road | Report |
412 |
| 2019-09-07 15:00:447th September 2019 |  Weymouth vs Welling United | 1 - 0 | Vanarama National League South | Bob Lucas Stadium | Report |
1034 |
| 2019-09-14 15:00:3314th September 2019 |  Welling United vs Wealdstone | 1 - 2 | Vanarama National League South | Park View Road | Report |
594 |
| 2019-09-28 15:00:5628th September 2019 |  Hungerford Town vs Welling United | 1 - 2 | Vanarama National League South | Bulpit Lane | Report |
284 |
| 2019-10-05 15:00:195th October 2019 |  Welling United vs Tavistock | 4 - 1 | Emirates FA Cup | Park View Road | Report |
- |
| 2019-10-12 15:00:0212th October 2019 |  Welling United vs Hampton & Richmond Borough | 0 - 1 | Vanarama National League South | Park View Road | Report |
- |
| 2019-10-19 15:00:4819th October 2019 |  Welling United vs Eastleigh | - | Emirates FA Cup | Park View Road | Report |
- |
