| Welling Town vs Kennington | 2019-07-13 13:00:01July 13, 2019 |   Welling Town vs Kennington | 4 - 2 | | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Phoenix Sports U23 | 2019-07-16 19:45:45July 16, 2019 |  Welling Town vs Phoenix Sports U23 | 2 - 1 | | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Ashford United | 2019-07-20 15:00:40July 20, 2019 |  Welling Town vs Ashford United | 2 - 3 | | 19/20 | Gallagher Stadium | Recap | - |
| Welling Town vs Cray Valley Paper Mills | 2019-07-23 19:45:11July 23, 2019 |  Welling Town vs Cray Valley Paper Mills | 0 - 3 | | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs SC Thamesmead | 2019-07-25 19:45:25July 25, 2019 |  Welling Town vs SC Thamesmead | 1 - 4 | | 19/20 | Bayliss Avenue | Recap | - |
| Croydon FC vs Welling Town | 2019-07-27 15:00:53July 27, 2019 |  Croydon FC vs Welling Town | 4 - 2 | | 19/20 | Harrow Road | Recap | - |
| Welling Town vs Canterbury City | 2019-08-03 15:00:08August 3, 2019 |  Welling Town vs Canterbury City | 0 - 0 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Fisher vs Welling Town | 2019-08-06 19:45:15August 6, 2019 |  Fisher vs Welling Town | 3 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | St Pauls Sports Ground | Recap | - |
| Welling Town vs AFC Uckfield Town | 2019-08-10 15:00:03August 10, 2019 |  Welling Town vs AFC Uckfield Town | 1 - 4 | FA CUP | 19/20 | Bayliss Avenue | Recap | - |
| Bearsted vs Welling Town | 2019-08-17 15:00:29August 17, 2019 |  Bearsted vs Welling Town | 1 - 3 | SEA PIONEER SCEFL PREMIER | 19/20 | Otham Sports Club | Recap | - |
| Welling Town vs Tunbridge Wells | 2019-08-21 19:45:31August 21, 2019 |  Welling Town vs Tunbridge Wells | 1 - 2 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Greenwich Borough | 2019-08-27 19:45:52August 27, 2019 |  Welling Town vs Greenwich Borough | 1 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Erith Town vs Welling Town | 2019-08-31 15:00:37August 31, 2019 |  Erith Town vs Welling Town | 2 - 2 | FA VASE | 19/20 | Erith Stadium | Recap | - |
| Welling Town vs Erith Town | 2019-09-04 19:45:29September 4, 2019 | Welling Town vs Erith Town | 2 - 0 | FA VASE | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Deal Town | 2019-09-07 15:00:05September 7, 2019 |  Welling Town vs Deal Town | 5 - 3 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Arundel vs Welling Town | 2019-09-14 15:00:10September 14, 2019 |  Arundel vs Welling Town | 1 - 7 | FA VASE | 19/20 | Mill Road | Recap | - |
| Corinthian vs Welling Town | 2019-09-17 19:45:17September 17, 2019 |  Corinthian vs Welling Town | 1 - 2 | SEA PIONEER SCEFL PREMIER | 19/20 | Gay Dawn Farm | Recap | - |
| Welling Town vs Welling United | 2019-09-24 19:45:51September 24, 2019 |  Welling Town vs Welling United | 1 - 2 | FRIENDLY | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Lordswood | 2019-09-28 15:00:25September 28, 2019 |  Welling Town vs Lordswood | 3 - 0 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| AFC Croydon Athletic vs Welling Town | 2019-10-05 15:00:25October 5, 2019 |  AFC Croydon Athletic vs Welling Town | 0 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | Mayfield Stadium | Recap | - |
| Welling Town vs Erith & Belvedere | 2019-10-12 15:00:27October 12, 2019 |  Welling Town vs Erith & Belvedere | 5 - 1 | FA VASE | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Glebe | 2019-10-19 15:00:24October 19, 2019 |  Welling Town vs Glebe | 2 - 4 | KENT SENIOR TROPHY | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Fisher | 2019-10-23 19:45:40October 23, 2019 | Welling Town vs Fisher | 0 - 0 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Sheppey United | 2019-10-26 15:00:04October 26, 2019 |  Welling Town vs Sheppey United | 3 - 2 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Welling Town vs Bedfont & Feltham | 2019-11-02 15:00:55November 2, 2019 |  Welling Town vs Bedfont & Feltham | 3 - 1 | FA VASE | 19/20 | Bayliss Avenue | Recap | - |
| Holmesdale vs Welling Town | 2019-11-06 19:30:04November 6, 2019 |  Holmesdale vs Welling Town | 4 - 3 | SCEFL CUP | 19/20 | Oakley Road | Recap | - |
| Welling Town vs Crowborough Athletic | 2019-11-09 15:00:17November 9, 2019 |  Welling Town vs Crowborough Athletic | 2 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Recap | - |
| Glebe vs Welling Town | 2019-11-16 15:00:24November 16, 2019 | Glebe vs Welling Town | 1 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | Foxbury Avenue | Recap | - |
| Punjab United vs Welling Town | 2019-11-23 15:00:43November 23, 2019 |  Punjab United vs Welling Town | 2 - 1 | SEA PIONEER SCEFL PREMIER | 19/20 | Elite Venue | Recap | - |
| Chatham Town vs Welling Town | 2019-11-30 15:00:43November 30, 2019 |  Chatham Town vs Welling Town | 1 - 0 | FA VASE | 19/20 | The Sports Ground | Recap | - |
| Beckenham Town vs Welling Town | 2019-12-07 15:00:25December 7, 2019 |  Beckenham Town vs Welling Town | 15:00:253:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Eden Park Avenue | Preview | - |
| Canterbury City vs Welling Town | 2019-12-14 15:00:15December 14, 2019 | Canterbury City vs Welling Town | 15:00:153:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Salters Lane FAVERSHAM | Preview | - |
| Welling Town vs Corinthian | 2019-12-21 15:00:06December 21, 2019 | Welling Town vs Corinthian | 15:00:063:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Greenwich Borough vs Welling Town | 2019-12-28 15:00:57December 28, 2019 | Greenwich Borough vs Welling Town | 15:00:573:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | The Mayplace Ground | Preview | - |
| Hollands & Blair vs Welling Town | 2020-01-04 15:00:02January 4, 2020 |  Hollands & Blair vs Welling Town | 15:00:023:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Star Meadow Sports Club | Preview | - |
| Welling Town vs AFC Croydon Athletic | 2020-01-11 15:00:59January 11, 2020 | Welling Town vs AFC Croydon Athletic | 15:00:593:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Welling Town vs K Sports | 2020-01-18 15:00:50January 18, 2020 |  Welling Town vs K Sports | 15:00:503:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Deal Town vs Welling Town | 2020-02-01 15:00:45February 1, 2020 | Deal Town vs Welling Town | 15:00:453:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | St Leonards Road | Preview | - |
| Crowborough Athletic vs Welling Town | 2020-02-08 15:00:43February 8, 2020 | Crowborough Athletic vs Welling Town | 15:00:433:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Crowborough Community Stadium | Preview | - |
| Welling Town vs Beckenham Town | 2020-02-15 15:00:38February 15, 2020 | Welling Town vs Beckenham Town | 15:00:383:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Chatham Town vs Welling Town | 2020-02-22 15:00:37February 22, 2020 | Chatham Town vs Welling Town | 15:00:373:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | The Sports Ground | Preview | - |
| Welling Town vs Punjab United | 2020-02-28 15:00:35February 28, 2020 | Welling Town vs Punjab United | 15:00:353:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Welling Town vs Bearsted | 2020-03-07 15:00:30March 7, 2020 | Welling Town vs Bearsted | 15:00:303:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Erith Town vs Welling Town | 2020-03-14 15:00:24March 14, 2020 | Erith Town vs Welling Town | 15:00:243:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Erith Stadium | Preview | - |
| Sheppey United vs Welling Town | 2020-03-21 15:00:26March 21, 2020 | Sheppey United vs Welling Town | 15:00:263:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | The Havill Stadium | Preview | - |
| Welling Town vs Erith & Belvedere | 2020-03-28 15:00:20March 28, 2020 | Welling Town vs Erith & Belvedere | 15:00:203:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Lordswood vs Welling Town | 2020-04-04 15:00:20April 4, 2020 | Lordswood vs Welling Town | 15:00:203:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Martyn Grove | Preview | - |
| K Sports vs Welling Town | 2020-04-10 15:00:19April 10, 2020 | K Sports vs Welling Town | 15:00:193:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | K Sports Cobdown | Preview | - |
| Welling Town vs Glebe | 2020-04-13 15:00:28April 13, 2020 | Welling Town vs Glebe | 15:00:283:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Tunbridge Wells vs Welling Town | 2020-04-18 15:00:27April 18, 2020 | Tunbridge Wells vs Welling Town | 15:00:273:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | The Culverden Stadium | Preview | - |
| Welling Town vs Hollands & Blair | 2020-04-25 15:00:18April 25, 2020 | Welling Town vs Hollands & Blair | 15:00:183:00 pm | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Welling Town vs Chatham Town | 2020-04-26 15:00:34April 26, 2020 | Welling Town vs Chatham Town | 15:00:34Postponed | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
| Erith & Belvedere vs Welling Town | 2020-04-27 15:00:59April 27, 2020 | Erith & Belvedere vs Welling Town | 15:00:59Postponed | SEA PIONEER SCEFL PREMIER | 19/20 | Park View Road | Preview | - |
| Welling Town vs Erith Town | 2020-04-28 15:00:44April 28, 2020 | Welling Town vs Erith Town | 15:00:44Postponed | SEA PIONEER SCEFL PREMIER | 19/20 | Bayliss Avenue | Preview | - |
