Fixtures are subject to change due to postponements and cup matches.
| Date | Team | Location | Type | Result | Scorers |
|---|---|---|---|---|---|
| 20.07.2019 | Hull City | Away | Pre-Season | ||
| 24.08.2019 | Doncaster | Away | Pre-Season | ||
| 31.08.2019 | Friendly – TBC | ||||
| 02.09.2019 | Bishopthorpe | Home | Pre-Season | ||
| 07.09.2019 | Rotherham | Home | Pre-Season | ||
| 12.09.2019 | York City Academy | Away | Pre-Season | ||
| 14.09.2019 | Tournament | East Riding | Tournament | L, L, W, D | Whitehead 2, Hobson, Garbutt-Smith |
| 21.09.2019 | East Riding | Away | League | L 5-3 | Whitehead, Garbutt-Smith, Thompson. |
| 28.09.2019 | Sheffield | Away | League | L 4-2 | Littlewood, Thompson |
| 05.10.2019 | Calderdale | Home | League | Pstpnd | |
| 12.10.2019 | Scarborough Rep | Away | Friendly | ||
| 19.10.2019 | Rotherham | Away | League | L 4-1 | Garbutt-Smith |
| 26.10.2019 | Wakefield | Home | League | Pstpnd | |
| 02.11.2019 | |||||
| 09.11.2019 | Harrogate | Home | ESFA Rd 2 | Pstpnd | |
| 16.11.2019 | Harrogate | Home | ESFA Rd 2 | W 7-1 | Thompson 3, Meek 2, Garbutt-Smith, Brown |
| 23.11.2019 | Wakefield | Home | League | W 5-1 | Brown, Thompson, Wakerley, Whitehead, Bajaziti |
| 30.11.2019 | Doncaster | Home | League | W 2-0 | Brown, Cottam |
| 07.12.2019 | Hartlepool | Away | ESFA Rd 3 | Pstpnd | |
| 14.12.2019 | Hull | Away | League | W 3-7 | Garbutt-Smith 2, Holowkiewicz 2, Littlewood, Thompson, Bryant |
| 21.12.2019 | Leeds | Home | League | W 3-0 | Armitage, Brown, Garbutt-Smith |
| 28.12.2019 | |||||
| 04.01.2020 | |||||
| 11.01.2020 | Hartlepool | Away | ESFA Rd 3 | L 7-1 | Holowkiewicz |
| 18.01.2020 | Barnsley | Home | League | Pstpnd | |
| 25.01.2020 | Sheffield | Away | League | W 3-4 | Brown 2, Meek, Garbutt-Smith |
| 01.02.2020 | Calderdale | Away | League | W 2-5 | Garbutt-Smith 2, Holowkiewicz, Whitehead, Dickinson |
| 08.02.2020 | Rotherham | Home | League | D 2-2 | Garbutt-Smith, Brown |
| 15.02.2020 | Wakefield | Away | League | ||
| 22.02.2020 | |||||
| 29.02.2020 | Barnsley | Away | West Yorks Cup Rd 2 | W 1-2 | Brown, Garbutt-Smith |
| 07.03.2020 | Barnsley | Home | League | W 6-2 | Brown 2, Cottam, Whitehead, Garbutt-Smith, Meek |
| 14.03.2020 | Spen Valley | Away | League | W 0-4 | Garbutt-Smith, Fort, Brown, Bajaziti |
| 14.03.2020 | Spen Valley | Home | League | W 3-0 | Littlewood, Brown, Meek |
| 21.03.2020 | Doncaster | Away | League | Pstpnd | |
| 28.03.2020 | Calderdale | Home | West Yorks Cup SF | Pstpnd | |
| 04.04.2020 | Barnsley | Away | League | ||
| 11.04.2020 | |||||
| 18.04.2020 | Leeds | Away | League | ||
| 25.04.2020 | Harrogate | Home | League | ||
| 02.05.2020 | |||||
| 09.05.2020 | |||||
| 16.05.2020 | |||||
| 23.05.2020 | |||||
| 30.05.2020 | |||||
| 06.06.2020 |