| Greencastle 5mile Road Race | ||
| Previous Winners | ||
| Overall | ||
| Year | Name/Club | Finish Time |
| 2022 | James Edgar (City of Lisburn AC) | 24:35 |
| 2021 | Conor Maguire (Monaghan Phoenix AC) | 24:53 |
| 2020 | Conor Duffy (Glaslough Harriers) | 24:35 |
| 2019 | Neil Johnston (Springwell) | 24:54 |
| 2018 | Mark McKinstry (North Belfast Harriers) | 24:42 |
| 2017 | Paul Pollock (Annadale Striders) | 24:31 |
| 2016 | Paul Pollock (Annadale Striders) | 24:52 |
| 2015 | Paul Pollock (Annadale Striders) | 24:24 |
| 2014 | Paul Pollock (Annadale Striders) | 24:07 (CR) |
| 2013 | Stephen Scullion (Clonliffe Harriers) | 25:10 |
| 2012 | Stephen Scullion (Clonliffe Harriers) | 24:57 |
| 2011 | Conor Bradley (City of Derry Spartans) | 25:36 |
| 2010 | Gareth Turnbull (St.Malachy's AC) | 24:39 |
| 2009 | Joe McAlister (St. Malachy's AC) | 25:25 |
| 2008 | Gareth Turnbull (St.Malachy's AC) | 24:14 |
| 2007 | Gareth Turnbull (St.Malachy's AC) | 24:21 |
| 2006 | Joe McAlister (St. Malachy's AC) | 25:15 |
| 2005 | Gareth Turnbull (St.Malachy's AC) | 24:24 |
| 2004 | Patrick Cassidy (Glaslough Harriers) | 25:52 |
| 2003 | Joe Byrne (Finn Valley AC) | 26:29 |
| 2002 | Paul Rowan (Willowfield Harriers) | 25:22 |
| 2001 | Dermott Kerr (Armagh AC) | 27:02 |
| 2000 | Donal Gallagher (Sparta) | 26:04 |
| 1999 | Simon Bell (Wellington AC) | 27:10 |
| 1998 | Donal Gallagher (Sparta) | 26:01 |
| 1997 | Donal Gallagher (Sparta) | 25:50 |
| 1996 | Donal Gallagher (Sparta) | 25:50 |
| 1995 | Donal Gallagher (Sparta) | 25:40 |
| 1994 | Damian Galvin (Coalisland) | 27:35 |
| 1993 | Donal Gallagher (Sparta) | 26:05 |
| 1992 | Donal Gallagher (Sparta) | 26:20 |
| 1991 | Donal Gallagher (Sparta) | 26:40 |
| 1990 | Dominic McCartan (Carrickmore) | 30:28 |
| 1989 | Pat McBride (Glenelly) | 30:06 |
| 1988 | Tommy Hughes (Ballinascreen AC) | 27:23 |
| 1987 | Benny Slane (Greencastle AC) | 27:22 |
| 1986 | Michael Drum (Omagh Harriers) | 28:00 |
| Ladies | ||
| Year | Name/Club | Finish Time |
| 2022 | Grace Carson ( Mid Ulster/Loughborough) | 27:37 (CR) |
| 2021 | Grace Carson (Mid Ulster/Loughborough | 28:23 |
| 2020 | Grace Carson (Mid Ulster/Loughborough) | 28:14 |
| 2019 | Emma Mitchel (Clonliffe Harriers) | 29:20 |
| 2018 | Emma Mitchel (Team Nike) | 28:28 |
| 2017 | Emma Mitchel (Queens University Belfast) | 28:28 |
| 2016 | Catherine Whoriskey (City of Derry Spartans) | 28:12 |
| 2015 | Anne Marie McGlynn (Letterkenny AC) | 28:00 |
| 2014 | Heather Foley (Co Down) | 30:44 |
| 2013 | Maria McCambridge (Letterkenny AC) | 28:25 |
| 2012 | Maria McCambridge (Letterkenny AC) | 28:18 |
| 2011 | Maria McCambridge (Dundrum South Dublin) | 29:21 |
| 2010 | Hayley Fourie | 34:28 |
| 2009 | Maria McCambridge (Dundrum South Dublin) | 28:46 |
| 2008 | Maria McCambridge (Dundrum South Dublin) | 28:25 |
| 2007 | Maria McCambridge (Dundrum South Dublin) | 28:28 |
| 2006 | Jill Shannon (Lagan Valley AC) | 28:50 |
| 2005 | Julie Butler (Omagh Harriers) | 29:38 |
| 2004 | Jill Shannon (Lagan Valley) | 29:44 |
| 2003 | Margarot Synott (Letterkenny AC) | 30:10 |
| 2002 | Maria Skelton (Lagan Valley AC) | 30:07 |
| 2001 | Sharon Hatch (Sparta) | 29:52 |
| 2000 | Teresa Duffy (Beachmount) | 29:01 |
| 1999 | Pauline Thom (Ballymena & Antrim AC) | 29:45 |
| 1998 | Julie Butler (Omagh Harriers) | 31:01 |
| 1997 | Hazel McCausland (Omagh Harriers) | 33:56 |
| 1996 | Olivia McCullagh (Sparta) | 34:40 |
| 1995 | Pauline Quinn (Ballymena & Antrim AC) | 29:29 |
| 1994 | Hazel Breen ( Omagh Harriers) | 32:01 |
| 1993 | Roisin Smyth (Sparta) | 30:56 |
| 1992 | Hazel Breen (Omagh Harriers) | 35:40 |
| 1991 | Hazel McCausland (Omagh Harriers) | 37:25 |
| 1990 | Hazel Breen (Omagh Harriers) | 32:50 |
| 1989 | Kate Cunningham (Omagh Harriers) | 34:40 |
| 1988 | Teresa Kidd (Ballinascreen AC) | 31:05 |
| 1987 | Teresa Kidd (Ballinascreen AC) | 31:30 |
| 1986 | Collete Woods (Omagh Harriers) | 34:00 |