| 2019-07-20 14:00:10July 20, 2019 | Glebe North Reserves vs Dollingstown Reserves | 1 - 3 | Pre Season | 2019/20 | |
| 2019-07-27 13:00:09July 27, 2019 | Glenavy vs Dollingstown Reserves | 1 - 7 | Pre Season | 2019/20 | |
| 2019-08-01 19:00:19August 1, 2019 | Dollingstown Reserves vs Crumlin United Reserves | 19:00:19Cancelled | Pre Season | 2019/20 | |
| 2019-08-08 18:30:12August 8, 2019 | Dollingstown Reserves vs Dromara Village Reserves | 3 - 0 | Pre Season | 2019/20 | |
| 2019-08-17 14:15:09August 17, 2019 | Dollingstown Reserves vs Moneyslane Reserves | 7 - 1 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-08-21 18:30:06August 21, 2019 | Ballymacash Rangers Reserves vs Dollingstown Reserves | 4 - 3 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-08-24 13:30:37August 24, 2019 | Armagh Rovers vs Dollingstown Reserves | 1 - 0 | The Marshall Cup | 2019/20 | |
| 2019-08-29 18:30:12August 29, 2019 | Dollingstown Reserves vs Portadown U20’s | 3 - 7 | Pre Season | 2019/20 | |
| 2019-09-14 13:30:16September 14, 2019 | Dollingstown Reserves vs Groomsport | 1 - 1 | The Fonacab Irish Junior Cup | 2019/20 | |
| 2019-09-20 20:15:29September 20, 2019 | Armagh City Reserves vs Dollingstown Reserves | 0 - 1 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-09-28 14:15:28September 28, 2019 | Banbridge Town Reserves vs Dollingstown Reserves | 0 - 12 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-10-05 14:00:41October 5, 2019 | Valley Rangers Reserves vs Dollingstown Reserves | 4 - 5 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-10-12 14:15:58October 12, 2019 | Tandragee Rovers Reserves vs Dollingstown Reserves | 1 - 7 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-10-19 14:00:08October 19, 2019 | Dollingstown Reserves vs Crieve Rovers | 7 - 0 | The Mid Ulster Shield | 2019/20 | |
| 2019-10-25 20:15:50October 25, 2019 | St. Mary’s Reserves vs Dollingstown Reserves | 1 - 2 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-11-09 13:30:15November 9, 2019 | Ballyoran vs Dollingstown Reserves | 3 - 1 | The Mid Ulster Shield | 2019/20 | |
| 2019-11-16 14:00:54November 16, 2019 | Dollingstown Reserves vs Rathfriland Rangers Reserves | 4 - 0 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-11-23 14:00:20November 23, 2019 | Moneyslane Reserves vs Dollingstown Reserves | 2 - 1 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2019-12-07 14:00:52December 7, 2019 | Dollingstown Reserves vs St. Mary’s Reserves | 9 - 0 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-01-04 13:30:13January 4, 2020 | Dollingstown Reserves vs Markethill Swifts Reserves | 6 - 0 | The Wilmor Johnston Memorial Cup | 2019/20 | |
| 2020-01-11 14:00:02January 11, 2020 | Hanover Reserves vs Dollingstown Reserves | 1 - 1 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-01-18 14:00:52January 18, 2020 | Coagh United Reserves vs Dollingstown Reserves | 2 - 1 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-02-01 14:00:25February 1, 2020 | Dollingstown Reserves vs Lurgan Town Reserves | 5 - 0 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-02-08 13:00:40February 8, 2020 | Dollingstown Reserves vs Newry City AFC U20’s | 5 - 1 | Pre Season | 2019/20 | |
| 2020-02-15 13:30:01February 15, 2020 | Dollingstown Reserves vs Richhill AFC Reserves | 13:30:01Postponed | The Wilmor Johnston Memorial Cup | 2019/20 | |
| 2020-02-22 14:15:43February 22, 2020 | Lurgan Town Reserves vs Dollingstown Reserves | 0 - 2 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-02-29 14:15:36February 29, 2020 | Dollingstown Reserves vs Richhill AFC Reserves | 3 - 2 | The Wilmor Johnston Memorial Cup | 2019/20 | |
| 2020-03-07 14:15:50March 7, 2020 | Rathfriland Rangers Reserves vs Dollingstown Reserves | 0 - 3 | Daily Mirror MUFL Reserve Championship | 2019/20 | |
| 2020-03-14 14:15:47March 14, 2020 | Dollingstown Reserves vs Armagh City Reserves | 14:15:47Postponed | Daily Mirror MUFL Reserve Championship | 2019/20 | |