| Friday 6th September 2019 | |
| Newry City U18 | Ards U18 |
| Friday 13th September 2019 | |
| Crusaders U18 | Newry City U18 |
| Friday 20th September 2019 | |
| Ballymena United U18 | Newry City U18 |
| Friday 27th September 2019 | |
| Newry City U18 | Carrick Rangers U18 |
| Friday 4th October 2019 | |
| Newry City U18 | Dungannon Swifts U18 |
| Friday 11th October 2019 | |
| Newry City U18 | Glentoran Colts |
| Friday 18th October 2019 | |
| Newry City U18 | Warrenpoint Town U18 |
| Friday 8th November 2019 | |
| Institute U18 | Newry City U18 |
| Friday 15th November 2019 | |
| Cliftonville Strollers | Newry City U18 |
| Friday 22nd November 2019 | |
| Newry City U18 | Coleraine U18 |
| Friday 6th December 2019 | |
| Newry City U18 | Ballinamallard United U18 |
| Friday 13th December 2019 | |
| Glenavon U18 | Newry City U18 |
| Friday 20th December 2019 | |
| Newry City U18 | Linfield Rangers |
| Friday 3rd January 2020 | |
| Newry City U18 | Crusaders U18 |
| Friday 17th January 2020 | |
| Carrick Rangers U18 | Newry City U18 |
| Friday 24th January 2020 | |
| Ards U18 | Newry City U18 |
| Friday 31st January 2020 | |
| Newry City U18 | Ballymena United U18 |
| Friday 7th February 2020 | |
| Linfield Rangers | Newry City U18 |
| Friday 14th February 2020 | |
| Warrenpoint Town U18 | Newry City U18 |
| Friday 28th February 2020 | |
| Newry City U18 | Institute U18 |
| Friday 6th March 2020 | |
| Newry City U18 | Cliftonville Strollers |
| Friday 13th March 2020 | |
| Coleraine U18 | Newry City U18 |
| Friday 20th March 2020 | |
| Dungannon Swifts U18 | Newry City U18 |
| Friday 27th March 2020 | |
| Newry City U18 | Glenavon U18 |
| Friday 3rd April 2020 | |
| Ballinamallard United U18 | Newry City U18 |
| Friday 10th April 2020 | |
| Glentoran Colts | Newry City U18 |