| 2019-07-13 15:00:52Jul 13, 2019 | Walthamstow  | 1 - 1 |  Heybridge Swifts | Friendly | N/A | Report |
| 2019-07-16 19:45:25Jul 16, 2019 | Walthamstow | 1 - 1 |  Enfield Borough | Friendly | N/A | Report |
| 2019-07-20 15:00:09Jul 20, 2019 | Walthamstow | 2 - 0 |  FC Romania | Friendly | N/A | Report |
| 2019-07-23 19:45:21Jul 23, 2019 | Walthamstow | 1 - 0 |  Canvey Island | Friendly | N/A | Report |
| 2019-07-25 19:45:16Jul 25, 2019 | Clapton CFC  | 1 - 2 | Walthamstow | Friendly | N/A | Report |
| 2019-07-27 15:00:59Jul 27, 2019 | Walthamstow | 0 - 0 |  Coggeshall Town | Friendly | N/A | Report |
| 2019-08-03 15:00:17Aug 3, 2019 | Walthamstow | 7 - 0 |  Tower Hamlets | Essex Senior League | N/A | Report |
| 2019-08-10 15:00:14Aug 10, 2019 | Walthamstow | 5 - 0 |  Sporting Bengal United | FA Cup | N/A | Report |
| 2019-08-17 15:00:17Aug 17, 2019 | Walthamstow | 1 - 0 |  Stansted | Essex Senior League | N/A | Report |
| 2019-08-24 15:00:48Aug 24, 2019 | Walthamstow | 2 - 0 |  Great Wakering Rovers | FA Cup | N/A | Report |
| 2019-08-27 19:45:40Aug 27, 2019 | Walthamstow | 1 - 1 |  Hadley | Essex Senior League | N/A | Report |
| 2019-09-08 15:00:39Sep 8, 2019 | Aylesbury United  | 0 - 3 | Walthamstow | FA Cup | N/A | Report |
| 2019-09-10 19:45:54Sep 10, 2019 | Walthamstow | 1 - 3 |  West Essex | Essex Senior Cup | N/A | Report |
| 2019-09-14 15:00:47Sep 14, 2019 | Buckhurst Hill  | 1 - 1 | Walthamstow | Essex Thameside Trophy | N/A | Report |
| 2019-09-17 19:45:52Sep 17, 2019 | Walthamstow | 2 - 0 |  Ilford | Essex Senior League | N/A | Report |
| 2019-09-21 15:00:44Sep 21, 2019 | Walthamstow | 1 - 1 |  Abbey Rangers | FA Cup | N/A | Report |
| 2019-09-24 19:45:53Sep 24, 2019 | Abbey Rangers | 2 - 1 | Walthamstow | FA Cup | N/A | Report |
| 2019-09-28 15:00:43Sep 28, 2019 | Walthamstow | 3 - 0 |  Cockfosters | Essex Senior League | N/A | Report |
| 2019-10-01 19:45:16Oct 1, 2019 | Walthamstow | 1 - 3 |  Hashtag United | Gordon Brasted Trophy | N/A | Report |
| 2019-10-08 19:45:54Oct 8, 2019 | St Margaretsbury  | 0 - 3 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-10-12 15:00:04Oct 12, 2019 | Broadfields United  | 1 - 3 | Walthamstow | FA Vase | N/A | Report |
| 2019-10-19 15:00:37Oct 19, 2019 | Walthamstow | 2 - 1 |  Redbridge | Essex Senior League | N/A | Report |
| 2019-10-22 19:45:20Oct 22, 2019 | Walthamstow | 3 - 0 | Tower Hamlets | Errington Challenge Cup | N/A | Report |
| 2019-10-26 15:00:52Oct 26, 2019 | Southend Manor  | 1 - 4 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-10-30 19:45:18Oct 30, 2019 | Enfield  | 1 - 7 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-11-02 15:00:22Nov 2, 2019 | Walthamstow | 2 - 3 |  AFC Uckfield Town | FA Vase | N/A | Report |
| 2019-11-09 15:00:22Nov 9, 2019 | Walthamstow | 0 - 0 |  Saffron Walden | Essex Senior League | N/A | Report |
| 2019-11-12 19:45:24Nov 12, 2019 | Walthamstow | 2 - 0 |  Woodford Town | Essex Senior League | N/A | Report |
| 2019-11-16 15:00:28Nov 16, 2019 | Tower Hamlets | 0 - 4 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-11-19 19:45:25Nov 19, 2019 | Walthamstow | 0 - 1 |  Takeley | Essex Senior League | N/A | Report |
| 2019-11-23 15:00:34Nov 23, 2019 | Walthamstow | 7 - 0 | Southend Manor | Essex Senior League | N/A | Report |
| 2019-11-26 19:45:28Nov 26, 2019 | St Margaretsbury | 0 - 2 | Walthamstow | Errington Challenge Cup | N/A | Report |
| 2019-11-30 15:00:10Nov 30, 2019 | Walthamstow | 0 - 1 | Hashtag United | Essex Senior League | N/A | Report |
| 2019-12-03 19:45:59Dec 3, 2019 | Walthamstow | 2 - 1 |  Hoddesdon Town | Essex Senior League | N/A | Report |
| 2019-12-07 15:00:15Dec 7, 2019 | West Essex | 2 - 4 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-12-14 15:00:46Dec 14, 2019 | Sporting Bengal United | 0 - 2 | Walthamstow | Essex Senior League | N/A | Report |
| 2019-12-28 14:00:59Dec 28, 2019 | Redbridge Reserves | 0 - 5 | Walthamstow | Peter Butcher Memorial Trophy | N/A | Report |
| 2020-01-04 15:00:26Jan 4, 2020 | Walthamstow | 2 - 1 |  Clapton | Essex Senior League | N/A | Report |
| 2020-01-11 15:00:51Jan 11, 2020 | Hoddesdon Town | 0 - 2 | Walthamstow | Essex Senior League | N/A | Report |
| 2020-01-22 19:45:57Jan 22, 2020 | Clapton | 2 - 6 | Walthamstow | Essex Senior League | N/A | Report |
| 2020-01-29 19:45:29Jan 29, 2020 | Ilford | 2 - 2 | Walthamstow | Essex Senior League | N/A | Report |
| 2020-02-01 15:00:47Feb 1, 2020 | Walthamstow | 0 - 2 | Cockfosters | Errington Challenge Cup | N/A | Report |
| 2020-02-04 19:45:16Feb 4, 2020 | Walthamstow | 6 - 1 |  Harlow Town Reserves | Peter Butcher Memorial Trophy | N/A | Report |
| 2020-02-08 15:00:16Feb 8, 2020 | Walthamstow | 4 - 0 |  Sawbridgeworth Town | Essex Senior League | N/A | Report |
| 2020-02-15 15:00:41Feb 15, 2020 | Hadley | 15:00:41Postponed | Walthamstow | Essex Senior League | N/A | Report |
| 2020-02-22 15:00:49Feb 22, 2020 | Takeley | 15:00:493:00 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-02-29 15:00:01Feb 29, 2020 | Walthamstow | 15:00:013:00 pm | Enfield | Essex Senior League | N/A | Preview |
| 2020-03-03 19:45:23Mar 3, 2020 | Walthamstow | 19:45:237:45 pm | Hadley | Peter Butcher Memorial Trophy | N/A | Preview |
| 2020-03-07 15:00:30Mar 7, 2020 | Saffron Walden | 15:00:303:00 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-03-10 19:45:26Mar 10, 2020 | Hashtag United | 19:45:267:45 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-03-14 15:00:46Mar 14, 2020 | Stansted | 15:00:463:00 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-03-17 19:45:00Mar 17, 2020 | Walthamstow | 19:45:007:45 pm | West Essex | Essex Senior League | N/A | Preview |
| 2020-03-24 19:45:47Mar 24, 2020 | East Thurrock United  | 19:45:477:45 pm | Walthamstow | Essex Thameside Trophy | N/A | Preview |
| 2020-03-28 15:00:45Mar 28, 2020 | Walthamstow | 15:00:453:00 pm | St Margaretsbury | Essex Senior League | N/A | Preview |
| 2020-03-31 19:45:51Mar 31, 2020 | Sawbridgeworth Town | 19:45:517:45 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-04-03 19:45:57Apr 3, 2020 | Woodford Town | 19:45:577:45 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-04-11 15:00:08Apr 11, 2020 | Redbridge | 15:00:083:00 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-04-18 15:00:59Apr 18, 2020 | Cockfosters | 15:00:593:00 pm | Walthamstow | Essex Senior League | N/A | Preview |
| 2020-04-25 15:00:55Apr 25, 2020 | Walthamstow | 15:00:553:00 pm | Sporting Bengal United | Essex Senior League | N/A | Preview |
