| 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 |
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| 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 | 0 - 0 | Emirates FA Cup | Park View Road | Report |
- |
| 2019-10-22 19:45:3022nd October 2019 | Eastleigh vs Welling United | 4 - 2 | Emirates FA Cup | | Report |
- |
| 2019-10-26 15:00:1726th October 2019 |  Welling United vs St Albans City | 0 - 1 | Vanarama National League South | Park View Road | Report |
- |
| 2019-10-29 19:45:2229th October 2019 |  Slough Town vs Welling United | 1 - 0 | Vanarama National League South | Arbour Park | Report |
- |
| 2019-11-02 15:00:482nd November 2019 |  Chippenham Town vs Welling United | 0 - 0 | Vanarama National League South | Hardenhuish Park | Report |
- |
| 2019-11-05 19:45:085th November 2019 |  Welling United vs Erith Town | 1 - 3 | London Senior Cup | Park View Road | Report |
- |
| 2019-11-12 19:45:3012th November 2019 |  Welling United vs Dulwich Hamlet | 0 - 0 | Vanarama National League South | Park View Road | Report |
- |
| 2019-11-16 15:00:2816th November 2019 |  Welling United vs Braintree Town | 6 - 2 | Vanarama National League South | Park View Road | Report |
- |
| 2019-11-23 15:00:1823rd November 2019 | Welling United vs St Albans City | 3 - 1 | Buildbase FA Trophy | Park View Road | Report |
- |
| 2019-11-30 15:00:2830th November 2019 |  Dorking vs Welling United | 2 - 0 | Vanarama National League South | Meadowbank Stadium | Report |
- |
| 2019-12-07 15:00:197th December 2019 |  Welling United vs Hemel Hempstead | 2 - 0 | Vanarama National League South | Park View Road | Report |
- |
| 2019-12-14 15:00:5614th December 2019 | Yeovil Town vs Welling United | 3 - 1 | Buildbase FA Trophy | Huish Park | Report |
- |
| 2019-12-26 13:00:5826th December 2019 |  Welling United vs Dartford | 0 - 3 | Vanarama National League South | Park View Road | Report |
- |
| 2019-12-28 15:00:4628th December 2019 | Eastbourne vs Welling United | 2 - 1 | Vanarama National League South | Priory Lane | Report |
- |
| 2020-01-01 15:00:281st January 2020 | Dartford vs Welling United | 4 - 0 | Vanarama National League South | Princes Park | Report |
- |
| 2020-01-04 15:00:024th January 2020 | Welling United vs Weymouth | 1 - 3 | Vanarama National League South | Park View Road | Report |
- |
| 2020-01-07 19:45:447th January 2020 |  Welling United vs Whitstable Town | 1 - 2 | Kent Senior Cup | Park View Road | Report |
- |
| 2020-01-11 15:00:0211th January 2020 | Wealdstone vs Welling United | 1 - 0 | Vanarama National League South | Grosvenor Vale | Report |
- |
| 2020-01-18 15:00:4618th January 2020 | Welling United vs Hungerford Town | - | Vanarama National League South | Park View Road | Report |
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