| Old Orchard Division Two |
| 07/09/2019 |
| 14:00 | Ballybofey United | 0 | vs | 4 | Drumbar United | More |
| Venue : Finn Valley Complex Referee : Gerald Devine (Pending) |
| 14:00 | Cappry Rovers | 1 | vs | 0 | Kilmacrennan Celtic | More |
| Venue : Cappry Park, Cappry Referee : Leo Devenney (Pending) |
| 14:00 | Castlefin Celtic | 1 | vs | 2 | Dunlewey Celtic | More |
| Venue : Parkview Castlefin Referee : Marty McGarrigle (Pending) |
| 14:00 | Cranford FC Reserves | 1 | vs | 3 | Drumkeen United | More |
| Venue : Cranford Park Referee : Colm McConigley (Pending) |
| 14:00 | Drumoghill Res | 4 | vs | 0 | Copany Rovers | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 14/09/2019 |
| 14:00 | Ballybofey United | 2 | vs | 1 | Cappry Rovers | More |
| Venue : Finn Valley Complex Referee : Brian O Kane (Pending) |
| 14:00 | Copany Rovers | 1 | vs | 5 | Castlefin Celtic | More |
| Venue : Killowen Park Laghey Referee : Frank Duff (Pending) |
| 14:00 | Dunlewey Celtic | 3 | vs | 1 | Cranford FC Reserves | More |
| Venue : Glentornan park - Dunlewey Referee : George Montgomery (Pending) |
| 14:00 | Kilmacrennan Celtic | 2 | vs | 1 | Drumoghill Res | More |
| Venue : Lurgy Park-Kilmacrennan Referee : James Malseed (Pending) |
| 21/09/2019 |
| 14:00 | Castlefin Celtic | 3 | vs | 3 | Kilmacrennan Celtic | More |
| Venue : Parkview Castlefin Referee : Patrick Martin (Pending) |
| 14:00 | Drumbar United | 1 | vs | 3 | Cappry Rovers | More |
| Venue : Brookfield Park, Drumbar Referee : Alister Gourley (Pending) |
| 14:00 | Drumkeen United | 3 | vs | 1 | Dunlewey Celtic | More |
| Venue : St. Patricks Park, Drumkeen Referee : Sean Ferry (Pending) |
| 14:00 | Drumoghill Res | 3 | vs | 1 | Ballybofey United | More |
| Venue : The Moss, Drumoghill Referee : Leo Devenney (Pending) |
| 28/09/2019 |
| 14:00 | Ballybofey United | 3 | vs | 2 | Castlefin Celtic | More |
| Venue : Finn Valley Complex Referee : George Montgomery (Pending) |
| 14:00 | Cappry Rovers | 1 | vs | 0 | Drumoghill Res | More |
| Venue : Cappry Park, Cappry Referee : Frank Duff (Pending) |
| 14:00 | Copany Rovers | 0 | vs | 3 | Drumkeen United | More |
| Venue : Killowen Park Laghey Referee : Brian O Kane (Pending) |
| 14:00 | Dunlewey Celtic | 1 | vs | 1 | Drumbar United | More |
| Venue : Glentornan park - Dunlewey Referee : Leo Devenney (Pending) |
| 14:00 | Kilmacrennan Celtic | 9 | vs | 2 | Cranford FC Reserves | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Sean Ferry (Pending) |
| 05/10/2019 |
| 14:00 | Castlefin Celtic | 0 | vs | 2 | Cappry Rovers | More |
| Venue : Parkview Castlefin Referee : Leo Devenney (Pending) |
| 14:00 | Cranford FC Reserves | 3 | vs | 2 | Ballybofey United | More |
| Venue : Cranford Park Referee : Marty McCauley (Pending) |
| 14:00 | Drumbar United | 2 | vs | 4 | Drumoghill Res | More |
| Venue : Brookfield Park, Drumbar Referee : Brian O Kane (Pending) |
| 14:00 | Drumkeen United | 3 | vs | 3 | Kilmacrennan Celtic | More |
| Venue : St. Patricks Park, Drumkeen Referee : Con McLaughlin (Pending) |
| 14:00 | Dunlewey Celtic | 9 | vs | 0 | Copany Rovers | More |
| Venue : Glentornan park - Dunlewey Referee : Sean Ferry (Pending) |
| 12/10/2019 |
| 14:00 | Ballybofey United | 0 | vs | 5 | Drumkeen United | More |
| Venue : Finn Valley Complex Referee : George Clinton (Pending) |
| 14:00 | Cappry Rovers | 2 | vs | 1 | Cranford FC Reserves | More |
| Venue : Cappry Park, Cappry Referee : Diego Rainey (Pending) |
| 14:00 | Copany Rovers | 3 | vs | 2 | Drumbar United | More |
| Venue : Killowen Park Laghey Referee : Gerald Devine (Pending) |
| 14:00 | Drumoghill Res | 4 | vs | 3 | Castlefin Celtic | More |
| Venue : The Moss, Drumoghill Referee : Zach McLoughlin (Pending) |
| 14:00 | Kilmacrennan Celtic | 2 | vs | 3 | Dunlewey Celtic | More |
| Venue : Lurgy Park-Kilmacrennan Referee : George Montgomery (Pending) |
| 19/10/2019 |
| 14:00 | Copany Rovers | 0 | vs | 1 | Kilmacrennan Celtic | More |
| Venue : Killowen Park Laghey Referee : Brian O Kane (Pending) |
| 14:00 | Cranford FC Reserves | 4 | vs | 3 | Drumoghill Res | More |
| Venue : Cranford Park Referee : Leo Devenney (Pending) |
| 14:00 | Drumbar United | 5 | vs | 1 | Castlefin Celtic | More |
| Venue : Brookfield Park, Drumbar Referee : George Clinton (Pending) |
| 14:00 | Drumkeen United | 3 | vs | 3 | Cappry Rovers | More |
| Venue : St. Patricks Park, Drumkeen Referee : Zach McLoughlin (Pending) |
| 14:00 | Dunlewey Celtic | 4 | vs | 1 | Ballybofey United | More |
| Venue : Glentornan park - Dunlewey Referee : Sean Ferry (Pending) |
| 02/11/2019 |
| 14:00 | Cappry Rovers | 5 | vs | 4 | Dunlewey Celtic | More |
| Venue : Cappry Park, Cappry Referee : Brian O Kane (Pending) |
| 14:00 | Castlefin Celtic | 3 | vs | 1 | Cranford FC Reserves | More |
| Venue : Parkview Castlefin Referee : Colm McConigley (Pending) |
| 14:00 | Drumoghill Res | 1 | vs | 2 | Drumkeen United | More |
| Venue : The Moss, Drumoghill Referee : George Clinton (Pending) |
| 14:00 | Kilmacrennan Celtic | 4 | vs | 0 | Drumbar United | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Con McLaughlin (Pending) |
| 09/11/2019 |
| 14:00 | Castlefin Celtic | 3 | vs | 2 | Drumkeen United | More |
| Venue : Parkview Castlefin Referee : Vincent McLoughlin (Pending) |
| 14:00 | Copany Rovers | 2 | vs | 8 | Cappry Rovers | More |
| Venue : Killowen Park Laghey Referee : Leo Devenney (Pending) |
| 14:00 | Drumbar United | 3 | vs | 0 | Cranford FC Reserves | More |
| Venue : Brookfield Park, Drumbar Referee : Marty McGarrigle (Pending) |
| 14:00 | Dunlewey Celtic | 2 | vs | 5 | Drumoghill Res | More |
| Venue : Glentornan park - Dunlewey Referee : Colm McConigley (Pending) |
| 14:00 | Kilmacrennan Celtic | 1 | vs | 5 | Ballybofey United | More |
| Venue : Finn Valley Centre Referee : George Montgomery (Pending) |
| 16/11/2019 |
| 14:00 | Cranford FC Reserves | 0 | vs | 3 | Copany Rovers | More |
| Venue : Cranford Park Referee : Sean O Donnell (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 0 | Drumbar United | More |
| Venue : St. Patricks Park, Drumkeen Referee : Brian O Kane (Pending) |
| 30/11/2019 |
| 14:00 | Copany Rovers | 2 | vs | 3 | Drumoghill Res | More |
| Venue : Killowen Park Laghey Referee : George Clinton (Pending) |
| 14:00 | Drumbar United | 0 | vs | 1 | Ballybofey United | More |
| Venue : Brookfield Park, Drumbar Referee : Brian O Kane (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 3 | Cranford FC Reserves | More |
| Venue : Cranford Park Referee : Mick Lagan (Pending) |
| 14:00 | Dunlewey Celtic | 1 | vs | 3 | Castlefin Celtic | More |
| Venue : Glentornan park - Dunlewey Referee : Marty McCauley (Pending) |
| 14:00 | Kilmacrennan Celtic | 3 | vs | 2 | Cappry Rovers | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Sean Ferry (Pending) |
| 07/12/2019 |
| 14:00 | Ballybofey United | 3 | vs | 0 | Copany Rovers | More |
| Venue : Finn Valley Complex Referee : Diego Rainey (Pending) |
| 11/01/2020 |
| 14:00 | Cranford FC Reserves | 1 | vs | 3 | Dunlewey Celtic | More |
| Venue : Cranford Park Referee : Sean Ferry (Pending) |
| 14:00 | Drumoghill Res | 1 | vs | 3 | Kilmacrennan Celtic | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 25/01/2020 |
| 14:00 | Ballybofey United | 3 | vs | 0 | Drumoghill Res | More |
| Venue : Finn Valley Complex Referee : Gerald Devine (Pending) |
| 14:00 | Copany Rovers | 1 | vs | 5 | Cranford FC Reserves | More |
| Venue : Killowen Park Laghey Referee : Andrew Mullen (Pending) |
| 14:00 | Dunlewey Celtic | 3 | vs | 5 | Drumkeen United | More |
| Venue : Glentornan park - Dunlewey Referee : Seimi Ferry (Pending) |
| 14:00 | Kilmacrennan Celtic | 4 | vs | 3 | Castlefin Celtic | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Liam McLaughlin (Pending) |
| 01/02/2020 |
| 14:00 | Castlefin Celtic | 1 | vs | 2 | Ballybofey United | More |
| Venue : Parkview Castlefin Referee : Gerald Devine (Pending) |
| 14:00 | Cranford FC Reserves | 2 | vs | 2 | Kilmacrennan Celtic | More |
| Venue : Cranford Park Referee : Seimi Ferry (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 2 | Copany Rovers | More |
| Venue : St. Patricks Park, Drumkeen Referee : Michael Connolly (Pending) |
| 14:00 | Drumoghill Res | 0 | vs | 2 | Cappry Rovers | More |
| Venue : The Moss, Drumoghill Referee : Leo Devenney (Pending) |
| 08/02/2020 |
| 14:00 | Cappry Rovers | 4 | vs | 0 | Ballybofey United | More |
| Venue : Cappry Park, Cappry Referee : Tony McNamee (Pending) |
| 14:00 | Castlefin Celtic | 4 | vs | 1 | Copany Rovers | More |
| Venue : Parkview Castlefin Referee : Brian O Kane (Pending) |
| 14:00 | Drumbar United | 2 | vs | 2 | Drumkeen United | More |
| Venue : Brookfield Park, Drumbar Referee : Marty McGarrigle (Pending) |
| 15/02/2020 |
| 14:00 | Kilmacrennan Celtic | 2 | vs | 3 | Drumkeen United | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Sean Ferry (Pending) |
| 29/02/2020 |
| 14:00 | Cappry Rovers | 3 | vs | 0 | Drumkeen United | More |
| Venue : Cappry Park, Cappry Referee : George Clinton (Pending) |
| 07/03/2020 |
| 14:00 | Ballybofey United | 1 | vs | 1 | Cranford FC Reserves | More |
| Venue : Finn Valley Complex Referee : Sean O Donnell (Pending) |
| 14:00 | Copany Rovers | 0 | vs | 1 | Dunlewey Celtic | More |
| Venue : Killowen Park Laghey Referee : Brian O Kane (Pending) |
| 14:00 | Drumoghill Res | 3 | vs | 2 | Drumbar United | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 18/07/2020 |
| 14:00 | Ballybofey United | 0 | vs | 1 | Dunlewey Celtic | More |
| Venue : Dreenan Ballybofey Referee : Brian O Kane (Pending) |
| 14:00 | Cappry Rovers | 5 | vs | 1 | Drumbar United | More |
| Venue : Cappry Park, Cappry Referee : Diego Rainey (Pending) |
| 22/07/2020 |
| 19:00 | Drumkeen United | 0 | vs | 0 | Ballybofey United | More |
| Venue : Dreenan Ballybofey Referee : Barry Hunter |
| 19:00 | Drumoghill Res | 1 | vs | 4 | Cranford FC Reserves | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 25/07/2020 |
| 14:00 | Kilmacrennan Celtic | 3 | vs | 1 | Copany Rovers | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Frank Duff (Pending) |
| 29/07/2020 |
| 19:00 | Cappry Rovers | 1 | vs | 0 | Castlefin Celtic | More |
| Venue : Cappry Park, Cappry Referee : Barry Hunter |
| 01/08/2020 |
| 14:00 | Castlefin Celtic | 4 | vs | 0 | Drumoghill Res | More |
| Venue : Parkview Castlefin Referee : John Coll (Pending) |
| 14:00 | Cranford FC Reserves | 0 | vs | 4 | Cappry Rovers | More |
| Venue : Cranford Park Referee : Leo Devenney (Pending) |
| 14:00 | Drumbar United | 4 | vs | 1 | Copany Rovers | More |
| Venue : Brookfield Park, Drumbar Referee : Liam McLaughlin (Pending) |
| 14:00 | Kilmacrennan Celtic | 3 | vs | 2 | Dunlewey Celtic | More |
| Venue : Lurgy Park-Kilmacrennan Referee : Sean Ferry (Pending) |
| 05/08/2020 |
| 19:30 | Kilmacrennan Celtic | 4 | vs | 2 | Ballybofey United | More |
| Venue : Flagpole Field, Rathmullan Referee : Barry Hunter |
| 08/08/2020 |
| 14:00 | Cappry Rovers | 5 | vs | 0 | Copany Rovers | More |
| Venue : Cappry Park, Cappry Referee : Sean O Donnell (Pending) |
| 14:00 | Cranford FC Reserves | 3 | vs | 1 | Drumbar United | More |
| Venue : Cranford Park Referee : George Montgomery (Pending) |
| 14:00 | Drumoghill Res | 3 | vs | 1 | Dunlewey Celtic | More |
| Venue : The Moss, Drumoghill Referee : Marty McGarrigle (Pending) |
| 12/08/2020 |
| 19:00 | Castlefin Celtic | 7 | vs | 0 | Drumbar United | More |
| Venue : Parkview Castlefin Referee : Barry Hunter |
| 15/08/2020 |
| 14:00 | Copany Rovers | 2 | vs | 5 | Ballybofey United | More |
| Venue : Killowen Park Laghey Referee : Tony McNamee (Pending) |
| 14:00 | Cranford FC Reserves | 6 | vs | 1 | Castlefin Celtic | More |
| Venue : Cranford Park Referee : Leo Devenney (Pending) |
| 14:00 | Drumbar United | 0 | vs | 3 | Kilmacrennan Celtic | More |
| Venue : Brookfield Park, Drumbar Referee : Brian O Kane (Pending) |
| 14:00 | Dunlewey Celtic | 5 | vs | 1 | Cappry Rovers | More |
| Venue : Glentornan park - Dunlewey Referee : Sean Ferry (Pending) |
| 22/08/2020 |
| 14:00 | Drumbar United | 3 | vs | 0 | Dunlewey Celtic | More |
| Venue : Brookfield Park, Drumbar Referee : Diego Rainey (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 3 | Drumoghill Res | More |
| Venue : St. Patricks Park, Drumkeen Referee : Con McLaughlin (Pending) |
| 01/09/2020 |
| 19:00 | Castlefin Celtic | 2 | vs | 2 | Drumkeen United | More |
| Venue : Parkview Castlefin Referee : Brian O Kane (Pending) |
