Records for Cupar 5:
| Category | Name | Club | Time | Year |
|---|---|---|---|---|
| Male | Jamie Crowe | Central AC | 23:51 | 2022 |
| Female | Elizabeth McColgan | Dundee Hawkhill H | 26:00 | 1998 |
| Male Vet | Terry Mitchell | Fife AC | 25:38 | 2000 |
| Female Vet | Janette Stevenson | Falkirk Victoria H | 29:32 | 2002 |
| Male U20 | Logan Rees | Fife AC | 25:43 | 2014 |
| Female U20 | Annabel Simpson | Fife AC | 28:27 | 2016 |
Record progression for 5 mile course:
| Category | Name | Club | Time | Year |
|---|---|---|---|---|
| Male | Max Colligan | Falkirk Victoria H | 24:58 | 1998 |
| Phil Mowbray | Hunters Bog Trotters | 24:39 | 1999 | |
| Derek Hawkins | Kilbarchan AAC | 24:04 | 2012 | |
| Robbie Simpson | Deeside Runners | 24:02 | 2014 | |
| Logan Rees | Fife AC | 24:02 | 2017 | |
| Jamie Crowe | Central AC | 23:51 | 2022 | |
| Female | Elizabeth McColgan | Dundee Hawkhill H | 26:00 | 1998 |
| Male Vet | Kevin McCue | Fife AC | 26:35 | 1998 |
| Terry Mitchell | Fife AC | 25:38 | 2000 | |
| Female Vet | Margaret McLaren | Fife AC | 33:17 | 1998 |
| Addy Gerrard | Lasswade AAC | 30:01 | 2000 | |
| Janette Stevenson | Falkirk Victoria H | 29:32 | 2002 | |
| Male U20 | Neil Gunstone | Dundee Hawkhill H | 26:15 | 1998 |
| Graeme Bee | Fife AC | 26:14 | 2000 | |
| Tom Cunningham | St Andrews U AC | 25:47 | 2008 | |
| Logan Rees | Fife AC | 25:43 | 2014 | |
| Logan Rees | Fife AC | 24:02 | 2017 | |
| Female U20 | Zoe Baxter | St Andrews U AC | 31:55 | 1998 |
| Hester Dix | St Andrews U AC | 30:41 | 2008 | |
| Annabel Simpson | Fife AC | 28:27 | 2016 |