| Preliminary Round - 03/08/19 @ 14:30 | Score | Round 1 - 07/08/19 @ 18:30 | Score | Round 2 - 26/08/19 @ 18:30 | Score | Quarter-Final 28/12/19 @ 13:30 | Score | Semi-Final | Score | Winner | Score |
|---|---|---|---|---|---|---|---|---|---|---|---|
| CPD Sychdyn | 0 | Bala Town | 2 | Buckley Town | 4 | Flint Town United | Walkover | Flint Town United | |||
| Brickfield Rangers | 3 | CPD Caerwys | 5 AET | Corwen | 0 | Plas Madoc | 25/03/20 | The Globe, Buckley | Kick Off : 19:30 | ||||
| Rhostyllen | 4 (2) | Mynydd Isa Spartans | 3 | Flint Town United | H | Ruthin Town | 1 | Gresford Athletc | |||
| Mold Alexandra | 4 (4) Pens | Chirk AAA | 2 | Mynydd Isa Spartans | H | Gresford Athletic | 3 | ||||
| Penyffordd Lions | 4 | Mold Alexandra | 3 | Castell Alun Colts | 0 | Cefn Druids | 0 | Buckley Town | |||
| Halkyn & Flint Mountain | 8 | New Brighton Villa | 1 | Ruthin Town | 3 | Buckley Town | 2 | 24/03/20 | Cae-y-Castell, Flint | Kick Off : 19:30 | |||
| Rhydymwyn | 1 | Holywell Town | 13 | Mold Alexandra | 5 | 4 | Mold Alexandra | ||||
| Plas Madoc | 3 | Bradley Park | 0 | Coedpoeth United | 3 | Brymbo | 3 | ||||
| Llay Welfare | 2 | Cefn Mawr Rangers | 1 | Holywell Town | 1 | ||||||
| Coedpoeth United | 3 | Brickfield Rangers | 6 | Gresford Athletic | 2 | ||||||
| Coedpoeth United | 3 | Brymbo | 5 | ||||||||
| Airbus UK Broughton | 0 | Saltney Town | 3 | ||||||||
| Lex XI | 0 | Plas Madoc | 2 | ||||||||
| Brymbo | 7 | Brickfield Rangers | 1 | ||||||||
| Halkyn & Flint Mountain | 2 | Cefn Druids | 3 | ||||||||
| Plas Madoc | 4 AET | CPD Caerwys | 0 | ||||||||
| Rhosllaneurchurgog | 0 | ||||||||||
| Castell Alun Colts | 6 |
NEWFA Challenge Cup Scoreboard
| Date | Home | Time/Results | Away | League | Season | Ground | Article |
|---|---|---|---|---|---|---|---|
| Buckley Town | 4 - 0 | Corwen | NEWFA Challenge Cup | 2020 | Recap | ||
| Cefn Druids | 0 - 2 | Buckley Town | NEWFA Challenge Cup | 2020 | Recap | ||
| Buckley Town | Mold Alex | NEWFA Challenge Cup | 2020 | Recap |
