| 1901 | Allan Miller | Kendal AAC | MV50 | 42 | 49:07 | 2010 |
| 1902 | Stephen Smithies | Calder Valley Fell Runners | MV40 | 44 | 49:07 | 2014 |
| 1903 | Jon Tinman | Rossendale Harriers & AC | MV50 | 37 | 49:07 | 2017 |
| 1904 | I. Rooke | Kendal Triathlon Club | M | 46 | 49:08 | 1984 |
| 1905 | Pauline Haworth | Keswick AC | F | 45 | 49:08 | 1984 |
| 1906 | Harry Jarrett | Cumberland Fell Runners | MV50 | 43 | 49:08 | 2005 |
| 1907 | Matthew Rooke | Black Combe Runners | M | 38 | 49:08 | 2017 |
| 1908 | C. Leventon | Mercia Fell Runners | M | 73 | 49:09 | 1988 |
| 1909 | J. Smith | Pudsey & Bramley AC | M | 102 | 49:09 | 1991 |
| 1910 | G. Denver | Chorley Athletic & Triathlon Club | M | 69 | 49:09 | 1996 |
| 1911 | Helen Diamantides | Carnethy Hill Running Club | F | 50 | 49:09 | 2004 |
| 1912 | David Ralphs | Newburgh Nomads | MV40 | 51 | 49:09 | 2006 |
| 1913 | Richard Hall | Unattached | MV40 | 51 | 49:09 | 2008 |
| 1914 | Garry Beardwood | Helm Hill Runners | M | 43 | 49:09 | 2010 |
| 1915 | Wayne Collins | Unattached | M | 41 | 49:09 | 2011 |
| 1916 | Bill Johnson | Calder Valley Fell Runners | MV40 | 38 | 49:10 | 2009 |
| 1917 | A. Howie | Rucksack Club | M | 61 | 49:11 | 1987 |
| 1918 | P. Weighton | Chorley Athletic & Triathlon Club | M | 70 | 49:11 | 1996 |
| 1919 | Colin Jennings | Garstang Running Club | MV40 | 41 | 49:11 | 2012 |
| 1920 | J. Roberts | Black Combe Runners | MV40 | 62 | 49:12 | 1987 |
| 1921 | A. Murray | Dulwich Runners AC | M | 80 | 49:12 | 1992 |
| 1922 | Anthony Labram | Eden Runners | M | 47 | 49:12 | 2002 |
| 1923 | Richard Watson | Black Combe Runners | M | 48 | 49:12 | 2013 |
| 1924 | S. Johnston | Ryhope | M | 58 | 49:13 | 1997 |
| 1925 | T. Keddie | Dark Peak Fell Runners | MV40 | 51 | 49:13 | 1998 |
| 1926 | Garry Owens | Northumberland Fell Runners | MV40 | 51 | 49:13 | 2004 |
| 1927 | Sharon Taylor | Bingley Harriers & AC | F | 42 | 49:13 | 2011 |
| 1928 | Sean Robinson | Howgill Harriers | M | 45 | 49:13 | 2014 |
| 1929 | Robert Crawford | Howgill Harriers | MV40 | 41 | 49:13 | 2016 |
| 1930 | P. Jones | Airienteers | M | 66 | 49:14 | 1986 |
| 1931 | Helen Fines | Calder Valley Fell Runners | F | 44 | 49:14 | 2010 |
| 1932 | Pauline Haworth | Keswick AC | F | 47 | 49:15 | 1983 |
| 1933 | G. Clayton | Ambleside AC | MV40 | 47 | 49:15 | 1984 |
| 1934 | C. Wilson | Keswick AC | MV40 | 103 | 49:15 | 1991 |
| 1935 | C. Wilson | Keswick AC | MV40 | 81 | 49:15 | 1992 |
| 1936 | L. Farnsworth | Clayton le Moors Harriers | MV40 | 75 | 49:15 | 1993 |
| 1937 | Gavin Thomas | Kendal AAC | MV40 | 52 | 49:15 | 2006 |
| 1938 | S. Perruzza | Kendal Triathlon Club | M | 75 | 49:16 | 1989 |
| 1939 | R. Isbister | Horwich RMI Harriers | M | 74 | 49:16 | 1989 |
| 1940 | Derek Ratcliffe | Rossendale Harriers & AC | MV40 | 53 | 49:16 | 2003 |
| 1941 | Andy Taylor | Holmfirth Harriers AC | M | 52 | 49:16 | 2004 |
| 1942 | William Procter | Helm Hill Runners | MV50 | 45 | 49:16 | 2010 |
| 1943 | Jane Reedy | Ambleside AC | F | 42 | 49:16 | 2012 |
| 1944 | Hazel Robinson | Ambleside AC | FV40 | 31 | 49:16 | 2015 |
| 1945 | J. Beatson | Copeland | M | 48 | 49:17 | 1983 |
| 1946 | S. Emery | Unattached | M | 71 | 49:17 | 1996 |
| 1947 | J. Rea | Cumberland Fell Runners | MV40 | 59 | 49:17 | 1997 |
| 1948 | N. Hindle | Altrincham & District AC | MV40 | 57 | 49:17 | 1999 |
| 1949 | Hazel Robinson | Dallam Running Club | F | 49 | 49:17 | 2007 |
| 1950 | Chris Fellows | Black Combe Runners | MV40 | 52 | 49:17 | 2008 |