| Old Orchard Division Two |
| 08/09/2018 |
| 14:00 | Drumbar FC | 1 | vs | 3 | Killdrum Tigers | More |
| Venue : Drumbar Referee : Johnny McBride (Pending) |
| 14:00 | Gweedore Celtic | 0 | vs | 3 | Fintown Harps AFC | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : Michael Lagan (Pending) |
| 14:00 | Milford United FC | 2 | vs | 3 | Drumoghill FC Res | More |
| Venue : Moyle View Park Milford Referee : Colm McConigley (Pending) |
| 15/09/2018 |
| 14:00 | Drumoghill FC Res | 1 | vs | 1 | Drumkeen United | More |
| Venue : The Moss Referee : Colm McConigley (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 5 | Milford United FC | More |
| Venue : Pairc Achla Fintown Referee : Zack McLaughlin (Pending) |
| 14:00 | Killdrum Tigers | 3 | vs | 0 | Gweedore Celtic | More |
| Venue : Kildrum Referee : Gerald Devine (Pending) |
| 22/09/2018 |
| 14:00 | Drumbar FC | 4 | vs | 2 | Drumkeen United | More |
| Venue : Drumbar Referee : Leo Devenney (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 3 | Drumoghill FC Res | More |
| Venue : Pairc Achla Fintown Referee : 66153 (Pending) |
| 14:00 | Gweedore Celtic | 4 | vs | 3 | Cappry Rovers | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : Colm McConigley (Pending) |
| 14:00 | Milford United FC | 2 | vs | 0 | Killdrum Tigers | More |
| Venue : Moyle View Park Milford Referee : Barry Hunter (Pending) |
| 29/09/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 3 | Milford United FC | More |
| Venue : Cappry Park Referee : 73827 (Pending) |
| 14:00 | Drumkeen United | 5 | vs | 1 | Gweedore Celtic | More |
| Venue : Drumkeen Referee : Michael Lagan (Pending) |
| 14:00 | Drumoghill FC Res | 2 | vs | 2 | Drumbar FC | More |
| Venue : The Moss Referee : Zack McLaughlin (Pending) |
| 14:00 | Killdrum Tigers | 5 | vs | 1 | Fintown Harps AFC | More |
| Venue : Kildrum Referee : Leo Devenney (Pending) |
| 13/10/2018 |
| 14:00 | Fintown Harps AFC | 4 | vs | 0 | Cappry Rovers | More |
| Venue : Pairc Achla Fintown Referee : George Clinton (Pending) |
| 14:00 | Gweedore Celtic | 3 | vs | 3 | Drumbar FC | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : 73827 (Pending) |
| 14:00 | Killdrum Tigers | 5 | vs | 1 | Drumoghill FC Res | More |
| Venue : Kildrum Referee : Frank Duff (Pending) |
| 20/10/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 3 | Killdrum Tigers | More |
| Venue : Cappry Park Referee : Colm McConigley (Pending) |
| 14:00 | Drumkeen United | 1 | vs | 2 | Fintown Harps AFC | More |
| Venue : Drumkeen Referee : Sean O Donnell (Pending) |
| 14:00 | Drumoghill FC Res | 3 | vs | 2 | Gweedore Celtic | More |
| Venue : The Moss Referee : Zack McLaughlin (Pending) |
| 02/11/2018 |
| 20:00 | Milford United FC | 3 | vs | 1 | Gweedore Celtic | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : Liam McLaughlin (Pending) |
| 03/11/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 4 | Drumoghill FC Res | More |
| Venue : Cappry Park Referee : Sean O Donnell (Pending) |
| 14:00 | Fintown Harps AFC | 4 | vs | 3 | Drumbar FC | More |
| Venue : Pairc Achla Fintown Referee : Barry Hunter (Pending) |
| 14:00 | Killdrum Tigers | 4 | vs | 0 | Drumkeen United | More |
| Venue : Kildrum Referee : Zack McLaughlin (Pending) |
| 10/11/2018 |
| 14:00 | Drumbar FC | 1 | vs | 2 | Milford United FC | More |
| Venue : Drumbar Referee : 73827 (Pending) |
| 14:00 | Drumkeen United | 1 | vs | 3 | Cappry Rovers | More |
| Venue : Drumkeen Referee : Gerald Devine (Pending) |
| 24/11/2018 |
| 14:00 | Cappry Rovers | 0 | vs | 1 | Drumbar FC | More |
| Venue : Cappry Park Referee : Gerald Devine (Pending) |
| 01/12/2018 |
| 14:00 | Cappry Rovers | 3 | vs | 2 | Drumkeen United | More |
| Venue : Cappry Park Referee : Zack McLaughlin (Pending) |
| 14:00 | Drumoghill FC Res | 0 | vs | 0 | Milford United FC | More |
| Venue : The Moss Referee : Brian O Kane (Pending) |
| 14:00 | Fintown Harps AFC | 2 | vs | 1 | Gweedore Celtic | More |
| Venue : Pairc Achla Fintown Referee : Sean O Donnell (Pending) |
| 14:00 | Killdrum Tigers | 5 | vs | 0 | Drumbar FC | More |
| Venue : Kildrum Referee : 66153 (Pending) |
| 08/12/2018 |
| 14:00 | Drumbar FC | 2 | vs | 2 | Drumoghill FC Res | More |
| Venue : Drumbar Referee : Diego Rainey (Pending) |
| 14:00 | Fintown Harps AFC | 1 | vs | 2 | Killdrum Tigers | More |
| Venue : Pairc Achla Fintown Referee : Zack McLaughlin (Pending) |
| 14:00 | Gweedore Celtic | 1 | vs | 2 | Drumkeen United | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : 73827 (Pending) |
| 14:00 | Milford United FC | 5 | vs | 1 | Cappry Rovers | More |
| Venue : Moyle View Park Milford Referee : Liam McConigley (Pending) |
| 05/01/2019 |
| 14:00 | Milford United FC | 2 | vs | 1 | Drumkeen United | More |
| Venue : Moyle View Park Milford Referee : Barry Hunter (Pending) |
| 12/01/2019 |
| 14:00 | Drumbar FC | 1 | vs | 5 | Cappry Rovers | More |
| Venue : Drumbar Referee : 66153 (Pending) |
| 14:00 | Drumkeen United | 3 | vs | 2 | Drumoghill FC Res | More |
| Venue : Drumkeen Referee : Con McLaughlin (Pending) |
| 14:00 | Gweedore Celtic | 0 | vs | 1 | Killdrum Tigers | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : Joe McHugh (Pending) |
| 14:00 | Milford United FC | 3 | vs | 5 | Fintown Harps AFC | More |
| Venue : Moyle View Park Milford Referee : Michael Lagan (Pending) |
| 19/01/2019 |
| 14:00 | Cappry Rovers | 5 | vs | 2 | Gweedore Celtic | More |
| Venue : Cappry Park Referee : Michael Lagan (Pending) |
| 14:00 | Drumkeen United | 4 | vs | 2 | Drumbar FC | More |
| Venue : Drumkeen Referee : Brian O Kane (Pending) |
| 14:00 | Drumoghill FC Res | 5 | vs | 5 | Fintown Harps AFC | More |
| Venue : The Moss Referee : Con McLaughlin (Pending) |
| 14:00 | Killdrum Tigers | 4 | vs | 3 | Milford United FC | More |
| Venue : Kildrum Referee : Gerald Devine (Pending) |
| 09/02/2019 |
| 14:00 | Fintown Harps AFC | 5 | vs | 0 | Drumkeen United | More |
| Venue : Pairc Achla Fintown Referee : George Clinton (Pending) |
| 14:00 | Gweedore Celtic | 2 | vs | 2 | Drumoghill FC Res | More |
| Venue : Screaban Industrial Estate Derrybeg Referee : Brian O Kane (Pending) |
| 14:00 | Killdrum Tigers | 2 | vs | 3 | Cappry Rovers | More |
| Venue : Kildrum Referee : Liam McConigley (Pending) |
| 14:00 | Milford United FC | 1 | vs | 0 | Drumbar FC | More |
| Venue : Rabs Park-Kerrykeel Referee : Seimi Ferry (Pending) |
| 16/02/2019 |
| 14:00 | Drumbar FC | 0 | vs | 5 | Fintown Harps AFC | More |
| Venue : Drumbar Referee : Colm McConigley (Pending) |
| 14:00 | Drumoghill FC Res | 0 | vs | 2 | Cappry Rovers | More |
| Venue : The Moss Referee : Seimi Ferry (Pending) |
| 23/02/2019 |
| 14:00 | Cappry Rovers | 2 | vs | 3 | Fintown Harps AFC | More |
| Venue : Cappry Park Referee : Frank Duff (Pending) |
| 02/03/2019 |
| 14:00 | Drumbar FC | 3 | vs | 0 | Gweedore Celtic | More |
| Venue : Drumbar Referee : George Clinton (Pending) |
| 14:00 | Drumoghill FC Res | 2 | vs | 3 | Killdrum Tigers | More |
| Venue : The Moss Referee : Con McLaughlin (Pending) |
| 16/03/2019 |
| 14:00 | Drumoghill FC Res | 0 | vs | 2 | Milford United FC | More |
| Venue : The Moss Referee : Zack McLaughlin (Pending) |
| 23/03/2019 |
| 12:00 | Milford United FC | 4 | vs | 1 | Gweedore Celtic | More |
| Venue : Moyle View Park Milford Referee : Zack McLaughlin (Pending) |
| 14:00 | Fintown Harps AFC | 1 | vs | 4 | Killdrum Tigers | More |
| Venue : Pairc Achla Fintown Referee : George Clinton (Pending) |
| 06/04/2019 |
| 14:00 | Drumkeen United | 0 | vs | 0 | Milford United FC | More |
| Venue : Drumkeen Referee : Liam McConigley (Pending) |
| 13/04/2019 |
| 14:00 | Milford United FC | 1 | vs | 1 | Drumoghill FC Res | More |
| Venue : Moyle View Park Milford Referee : Brian O Kane (Pending) |
| 16/04/2019 |
| 19:00 | Killdrum Tigers | 6 | vs | 1 | Fintown Harps AFC | More |
| Venue : Kildrum Referee : Mick Lagan (Pending) |
| 27/04/2019 |
| 14:00 | Drumkeen United | 0 | vs | 3 | Killdrum Tigers | More |
| Venue : Drumkeen Referee : George Clinton (Pending) |
| 11/05/2019 |
| 18:00 | Killdrum Tigers | 3 | vs | 1 | Milford United FC | More |
| Venue : Drumoghill FC Referee : TBC (Pending) |
