| Old Orchard Division Two |
| 08/09/2018 |
| 14:00 | Drumbar United | 1 | vs | 3 | Kildrum Tigers | More |
| Venue : Brookfield Park, Drumbar Referee : Ramelton Myles Mulgree (Pending) |
| 14:00 | Gweedore Celtic | 0 | vs | 3 | Fintown Harps AFC | More |
| Venue : An Screaban, Gweedore Referee : Barry Maxwell (Pending) |
| 14:00 | Milford United | 2 | vs | 3 | Drumoghill Res | More |
| Venue : Moyle View Park Milford Referee : Colm McConigley (Pending) |
| 15/09/2018 |
| 14:00 | Drumoghill Res | 1 | vs | 1 | Drumkeen United | More |
| Venue : The Moss, Drumoghill Referee : Colm McConigley (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 5 | Milford United | More |
| Venue : Páirc Acla, Fintown Referee : Zach McLoughlin (Pending) |
| 14:00 | Kildrum Tigers | 3 | vs | 0 | Gweedore Celtic | More |
| Venue : Station Road, Kildrum Referee : Gerald Devine (Pending) |
| 22/09/2018 |
| 14:00 | Drumbar United | 4 | vs | 2 | Drumkeen United | More |
| Venue : Brookfield Park, Drumbar Referee : Leo Devenney (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 3 | Drumoghill Res | More |
| Venue : Páirc Acla, Fintown Referee : 66153 (Pending) |
| 14:00 | Gweedore Celtic | 4 | vs | 3 | Cappry Rovers | More |
| Venue : An Screaban, Gweedore Referee : Colm McConigley (Pending) |
| 14:00 | Milford United | 2 | vs | 0 | Kildrum Tigers | More |
| Venue : Moyle View Park Milford Referee : Barry Hunter (Pending) |
| 29/09/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 3 | Milford United | More |
| Venue : Cappry Park, Cappry Referee : 73827 (Pending) |
| 14:00 | Drumkeen United | 5 | vs | 1 | Gweedore Celtic | More |
| Venue : St. Patricks Park, Drumkeen Referee : Barry Maxwell (Pending) |
| 14:00 | Drumoghill Res | 2 | vs | 2 | Drumbar United | More |
| Venue : The Moss, Drumoghill Referee : Zach McLoughlin (Pending) |
| 14:00 | Kildrum Tigers | 5 | vs | 1 | Fintown Harps AFC | More |
| Venue : Station Road, Kildrum Referee : Leo Devenney (Pending) |
| 13/10/2018 |
| 14:00 | Fintown Harps AFC | 4 | vs | 0 | Cappry Rovers | More |
| Venue : Páirc Acla, Fintown Referee : George Clinton (Pending) |
| 14:00 | Gweedore Celtic | 3 | vs | 3 | Drumbar United | More |
| Venue : An Screaban, Gweedore Referee : 73827 (Pending) |
| 14:00 | Kildrum Tigers | 5 | vs | 1 | Drumoghill Res | More |
| Venue : Station Road, Kildrum Referee : Frank Duff (Pending) |
| 20/10/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 3 | Kildrum Tigers | More |
| Venue : Cappry Park, Cappry Referee : Colm McConigley (Pending) |
| 14:00 | Drumkeen United | 1 | vs | 2 | Fintown Harps AFC | More |
| Venue : St. Patricks Park, Drumkeen Referee : Sean O Donnell (Pending) |
| 14:00 | Drumoghill Res | 3 | vs | 2 | Gweedore Celtic | More |
| Venue : The Moss, Drumoghill Referee : Zach McLoughlin (Pending) |
| 02/11/2018 |
| 20:00 | Milford United | 3 | vs | 1 | Gweedore Celtic | More |
| Venue : An Screaban, Gweedore Referee : Liam McLaughlin (Pending) |
| 03/11/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 4 | Drumoghill Res | More |
| Venue : Cappry Park, Cappry Referee : Sean O Donnell (Pending) |
| 14:00 | Fintown Harps AFC | 4 | vs | 3 | Drumbar United | More |
| Venue : Páirc Acla, Fintown Referee : Barry Hunter (Pending) |
| 14:00 | Kildrum Tigers | 4 | vs | 0 | Drumkeen United | More |
| Venue : Station Road, Kildrum Referee : Zach McLoughlin (Pending) |
| 10/11/2018 |
| 14:00 | Drumbar United | 1 | vs | 2 | Milford United | More |
| Venue : Brookfield Park, Drumbar Referee : 73827 (Pending) |
| 14:00 | Drumkeen United | 1 | vs | 3 | Cappry Rovers | More |
| Venue : St. Patricks Park, Drumkeen Referee : Gerald Devine (Pending) |
| 24/11/2018 |
| 14:00 | Cappry Rovers | 0 | vs | 1 | Drumbar United | More |
| Venue : Cappry Park, Cappry Referee : Gerald Devine (Pending) |
| 01/12/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 2 | Drumkeen United | More |
| Venue : Cappry Park, Cappry Referee : Zach McLoughlin (Pending) |
| 14:00 | Drumoghill Res | 0 | vs | 0 | Milford United | More |
| Venue : The Moss, Drumoghill Referee : Brian O Kane (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 1 | Gweedore Celtic | More |
| Venue : Páirc Acla, Fintown Referee : Sean O Donnell (Pending) |
| 14:00 | Kildrum Tigers | 5 | vs | 0 | Drumbar United | More |
| Venue : Station Road, Kildrum Referee : 66153 (Pending) |
| 08/12/2018 |
| 14:00 | Drumbar United | 2 | vs | 2 | Drumoghill Res | More |
| Venue : Brookfield Park, Drumbar Referee : Diego Rainey (Pending) |
| 14:00 | Fintown Harps AFC | 1 | vs | 2 | Kildrum Tigers | More |
| Venue : Páirc Acla, Fintown Referee : Zach McLoughlin (Pending) |
| 14:00 | Gweedore Celtic | 1 | vs | 2 | Drumkeen United | More |
| Venue : An Screaban, Gweedore Referee : 73827 (Pending) |
| 14:00 | Milford United | 5 | vs | 1 | Cappry Rovers | More |
| Venue : Moyle View Park Milford Referee : Liam McConigley (Pending) |
| 05/01/2019 |
| 14:00 | Milford United | 2 | vs | 1 | Drumkeen United | More |
| Venue : Moyle View Park Milford Referee : Barry Hunter (Pending) |
| 12/01/2019 |
| 14:00 | Drumbar United | 1 | vs | 5 | Cappry Rovers | More |
| Venue : Brookfield Park, Drumbar Referee : 66153 (Pending) |
| 14:00 | Drumkeen United | 3 | vs | 2 | Drumoghill Res | More |
| Venue : St. Patricks Park, Drumkeen Referee : Con McLaughlin (Pending) |
| 14:00 | Gweedore Celtic | 0 | vs | 1 | Kildrum Tigers | More |
| Venue : An Screaban, Gweedore Referee : 9523 (Pending) |
| 14:00 | Milford United | 3 | vs | 5 | Fintown Harps AFC | More |
| Venue : Moyle View Park Milford Referee : Barry Maxwell (Pending) |
| 19/01/2019 |
| 14:00 | Cappry Rovers | 5 | vs | 2 | Gweedore Celtic | More |
| Venue : Cappry Park, Cappry Referee : Barry Maxwell (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 2 | Drumbar United | More |
| Venue : St. Patricks Park, Drumkeen Referee : Brian O Kane (Pending) |
| 14:00 | Drumoghill Res | 5 | vs | 5 | Fintown Harps AFC | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 14:00 | Kildrum Tigers | 4 | vs | 3 | Milford United | More |
| Venue : Station Road, Kildrum Referee : Gerald Devine (Pending) |
| 09/02/2019 |
| 14:00 | Fintown Harps AFC | 5 | vs | 0 | Drumkeen United | More |
| Venue : Páirc Acla, Fintown Referee : George Clinton (Pending) |
| 14:00 | Gweedore Celtic | 2 | vs | 2 | Drumoghill Res | More |
| Venue : An Screaban, Gweedore Referee : Brian O Kane (Pending) |
| 14:00 | Kildrum Tigers | 2 | vs | 3 | Cappry Rovers | More |
| Venue : Station Road, Kildrum Referee : Liam McConigley (Pending) |
| 14:00 | Milford United | 1 | vs | 0 | Drumbar United | More |
| Venue : Rabs Park-Kerrykeel Referee : Seimi Ferry (Pending) |
| 16/02/2019 |
| 14:00 | Drumbar United | 0 | vs | 5 | Fintown Harps AFC | More |
| Venue : Brookfield Park, Drumbar Referee : Colm McConigley (Pending) |
| 14:00 | Drumoghill Res | 0 | vs | 2 | Cappry Rovers | More |
| Venue : The Moss, Drumoghill Referee : Seimi Ferry (Pending) |
| 23/02/2019 |
| 14:00 | Cappry Rovers | 2 | vs | 3 | Fintown Harps AFC | More |
| Venue : Cappry Park, Cappry Referee : Frank Duff (Pending) |
| 02/03/2019 |
| 14:00 | Drumbar United | 3 | vs | 0 | Gweedore Celtic | More |
| Venue : Brookfield Park, Drumbar Referee : George Clinton (Pending) |
| 14:00 | Drumoghill Res | 2 | vs | 3 | Kildrum Tigers | More |
| Venue : The Moss, Drumoghill Referee : Con McLaughlin (Pending) |
| 16/03/2019 |
| 14:00 | Drumoghill Res | 0 | vs | 2 | Milford United | More |
| Venue : The Moss, Drumoghill Referee : Zach McLoughlin (Pending) |
| 23/03/2019 |
| 12:00 | Milford United | 4 | vs | 1 | Gweedore Celtic | More |
| Venue : Moyle View Park Milford Referee : Zach McLoughlin (Pending) |
| 14:00 | Fintown Harps AFC | 1 | vs | 4 | Kildrum Tigers | More |
| Venue : Páirc Acla, Fintown Referee : George Clinton (Pending) |
| 06/04/2019 |
| 14:00 | Drumkeen United | 0 | vs | 0 | Milford United | More |
| Venue : St. Patricks Park, Drumkeen Referee : Liam McConigley (Pending) |
| 13/04/2019 |
| 14:00 | Milford United | 1 | vs | 1 | Drumoghill Res | More |
| Venue : Moyle View Park Milford Referee : Brian O Kane (Pending) |
| 16/04/2019 |
| 19:00 | Kildrum Tigers | 6 | vs | 1 | Fintown Harps AFC | More |
| Venue : Station Road, Kildrum Referee : Mick Lagan (Pending) |
| 27/04/2019 |
| 14:00 | Drumkeen United | 0 | vs | 3 | Kildrum Tigers | More |
| Venue : St. Patricks Park, Drumkeen Referee : George Clinton (Pending) |
| 11/05/2019 |
| 18:00 | Kildrum Tigers | 3 | vs | 1 | Milford United | More |
| Venue : Drumoghill FC Referee : TBC (Pending) |
