| YEAR | INDIVIDUAL CHAMPION | TIME AND COURSE | TEAMCHAMPION | PTS |
| 2025 | Jack Stein, Pomona-Pitzer | 24:33.5 @ Pomona College Wash course (8k) | Pomona-Pitzer | 29 |
| 2024 | Adam Sage, Claremont-M-S | 24:20.1 @ Carbon Canyon Park (8k) | Pomona-Pitzer | 24 |
| 2023 | Lucas Florsheim, Pomona-Pitzer | 24:44.3 @ Riverside City XC Course (8k) | Pomona-Pitzer | 23 |
| 2022 | Derek Fearon, Pomona-Pitzer | 24:44.8 @ Pomona College Wash course (8k) | Pomona-Pitzer | 21 |
| 2021 | Henry Pick, Claremont-M-S | 24:24.7 @ Pomona College Wash course (8k) | Pomona-Pitzer | 34 |
| 2020 | No meet | No meet | No meet | |
| 2019 | Thomas D'Anieri, Claremont-M-S | 24:51.88 @ Pomona College Wash course (8k) | Claremont-M-S | 31 |
| 2018 | Andy Reischling, Pomona-Pitzer | 25:52.6 @ Prado Park, Chino (8k) | Pomona-Pitzer | 23 |
| 2017 | Andy Reischling, Pomona-Pitzer | 25:33.71 @ Prado Park, Chino (8k) | Pomona-Pitzer | 32 |
| 2016 | Julian Sandoval, Whittier | 25:48.77 @ Prado Park, Chino (8k) | Claremont-M-S | 47 |
| 2015 | John Fowler, Pomona-Pitzer | 25:38.58 @ Prado Park, Chino (8k) | Claremont-M-S | 29 |
| 2014 | John Guzman, Occidental | 25:51.55 @ Prado Park, Chino (8k) | Claremont-M-S | 42 |
| 2013 | John Guzman, Occidental | 25:30.19 @ Prado Park, Chino (8k) | Claremont-M-S | 51 |
| 2012 | Rafer Dannenhauer, Claremont-M-S | 25:56.37 @ Prado Park, Chino (8k) | Claremont-M-S | 33 |
| 2011 | Eric Kleinsasser, Occidental | 25:37.45 @ Prado Park, Chino (8k) | Occidental | 47 |
| 2010 | Eric Kleinsasser, Occidental | 25:53.23 @ Prado Park, Chino (8k) | Claremont-M-S | 32 |
| 2009 | Eric Kleinsasser, Occidental | 25:24.47 @ Prado Park, Chino (8k) | Claremont-M-S | 33 |
| 2008 | Eric Kleinsasser, Occidental | 25:43.15 @ Prado Park, Chino (8k) | Claremont-M-S | 37 |
| 2007 | Kevin Chaves, Occidental | 26:23.92 @ La Mirada Park (8k) | Occidental | 27 |
| 2006 | Will Leer, Pomona-Pitzer | 24:51.0 @ Prado Park, Chino (8k) | Occidental | 34 |
| 2005 | Crosby Freeman, Pomona-Pitzer | 25:04.5 @ Prado Park, Chino (8k) | Pomona-Pitzer | 27 |
| 2004 | Crosby Freeman, Pomona-Pitzer | 25:36.3 @ Prado Park, Chino (8k) | Pomona-Pitzer | 36 |
| 2003 | Crosby Freeman, Pomona-Pitzer | 26:17.0 @ La Mirada Park (8k) | Pomona-Pitzer | 30 |
| 2002 | Pat McGrail, Claremont-M-S | 25:44 @ Prado Park, Chino (8k) | Claremont-M-S | 22 |
| 2001 | David Juiliano, Claremont-M-S | 25:54.8 @ Prado Park, Chino (8k) | Claremont-M-S | 18 |
| 2000 | Eli Klovee-Smith, Claremont-M-S | 26:32.9 @ Prado Park, Chino (8k) | Claremont-M-S | 27 |
| 1999 | Matthew Stuart, Whittier | 26:52.2 @ Prado Park, Chino (8k) | Claremont-M-S | 37 |
| 1998 | Juan Rodriguez, Whittier | 26:42 @ Prado Park, Chino (8k) | Claremont-M-S | 28 |
| 1997 | Ken Reed, Redlands | 27:54 @ Prado Park, Chino (8k) | Claremont-M-S | 46 |
| 1996 | Dan Kleiman, Caltech | 25:50 @ Prado Park, Chino (8k) | Claremont-M-S | 52 |
| 1995 | Will Allan, Occidental | 26:34 @ Prado Park, Chino (8k) | Occidental | 38 |
| 1994 | Will Allan, Occidental | 25:43 @ Prado Park, Chino (8k) | Occidental | 37 |
| 1993 | Avo Artinyan, Pomona-Pitzer | 26:00.9 @ Prado Park, Chino (8k) | Claremont-M-S | 49 |
| 1992 | Jose Garcia, Occidental | 25:56 @ Prado Park, Chino (8k) | Occidental | 40 |
| 1991 | Emmet Hogan, Occidental | 25:11 @ La Mirada Park (8k) | Occidental | 33 |
| 1990 | Marcial Beltran, Occidental | 25:25 @ La Mirada Park (8k) | Occidental | 19 |
| 1989 | Carl Berg, Claremont-M-S | 25:48 @ La Mirada Park (8k) | Claremont-M-S | 26 |
| 1988 | Chris Tregillis, Occidental | 25:43.7 @ Castaic Lake (8k) | Occidental | 22 |
| 1987 | Lionel Shaw, Occidental | 26:28.1 @ La Mirada Park | Occidental/PomonaPitzer | 31 |
| 1986 | Mike Scott, Claremont-M-S | 26:23.1 @ La Mirada Park (8k) | Occidental | 33 |
| 1985 | Brian Butterfield, Occidental | 26:18.9 @ La Mirada Park (8k) | Occidental | 22 |
| 1984 | Rory Frampton, Pomona-Pitzer | 27:34 @ Whittier College | Occidental | 26 |
| 1983 | David Francis, Pomona-Pitzer | 23:37 @ Redlands (4.7 miles) | Occidental | 28 |
| 1982 | Sieg Lindstrom, Pomona-Pitzer | 24:45 @ Whittier College | Pomona-Pitzer | 19 |
| 1981 | Sieg Lindstrom, Pomona-Pitzer | 24:16 @ Occidental | Pomona-Pitzer | 19 |
| 1980 | Don Wielenga, Occidental | 26:22 @ Puddingstone, Bonelli Park | Pomona-Pitzer | 23 |
| 1979 | Nick Buchan, Pomona-Pitzer | 26:12 @ Puddingstone, Bonelli Park | Pomona-Pitzer | 27 |
| 1978 | Gerry Harnett, Pomona-Pitzer | 24:19 @ Lower Arroyo, Pasadena (4.56 miles) | Occidental | 31 |
| 1977 | Tom Colley, Occidental | 26:23 @ Whittier | Occidental | 17 |
| 1976 | John Armstrong, Pomona-Pitzer | 23:09 @ Redlands Univ. | Occidental | 28 |
| 1975 | John Armstrong, Pomona-Pitzer | 22:10 @ Pomona College | Occidental | 24 |
| 1974 | Pat Kennedy, Occidental | 21:29 @ Occidental | Occidental/PomonaPitzer | 20 |
| 1973 | Randy Spotts, Redlands | 23:55 @ Puddingstone, Bonelli Park - story | Occidental | 28 |
| 1972 | Joel Jamison, Occidental | 25:31 @ Mt. SAC | Occidental | 22 |
| 1971 | Martins Ande, Occidental | 26:36 @ Mt. SAC (5.0 miles) | Occidental | 32 |
| 1970 | Adrian Jones, Redlands | 21:01 @ Whittier College (4.0 miles) | Occidental | 33 |
| 1969 | Alan Rude, Occidental | 24:35 @ Redlands (4.78 miles) | Occidental | 26 |
| 1968 | Bob Dienes, Occidental | 22:58 @ Mt. SAC (4.25 miles) | Occidental | 25 |
| 1967 | Bob Dienes, Occidental | 20:33 @ Mt. SAC (4.0 miles) | Occidental | 16 |
| 1966 | Ray Celaya, Occidental | 20:52 @ Mt. SAC (4.0 miles) | Occidental | 23 |
| 1965 | Steve Roulac, Pomona | 18:23 @ ? (3.8 miles) | Occidental | |
| 1964 | Bill Anderson, Occidental | 20:34 @ Mt. SAC | Redlands | 26 |
| 1963 | Gary Larson, Redlands | 22:01 @ Mt. SAC (4.0 miles) | Redlands | 21 |
| 1962 | Bill Anderson, Occidental | 18:57 @ Mt. SAC (3.7 miles) | Occidental | 15 |
| 1961 | Richard Jones, Occidental | 18:58 @ Mt. SAC (3.75 miles) | Occidental | 17 |
| 1960 | Ed Laughton, Claremont-Mudd | ? @ Whittier (4.0 miles) | Occidental | 21 |
| 1959 | Bill Peck, Occidental | ? @ Redlands | Occidental | 28 |
| 1958 | Bill Peck, Occidental | 21:53 @ Whittier (4.0 miles) | Occidental | 23 |
| 1957 | Don Perez, Whittier | 20:57 @ Mt. SAC (4.0 miles) | Occidental | 24 |
| 1956 | John Kerr, Occidental | 20:19 @ Mt. SAC (4.0 miles) | Occidental | 16 |
| 1955 | Ed Lingan, Occidental | 20:36 @ Mt. SAC (4.1 miles) | Occidental | 15 |
| 1954 | Larry Wray, Occidental | 19:14 @ Whittier (3.0 miles) | Occidental | 19 |
| 1953 | Russ Bonham, Whittier | 21:53 @ Caltech (4.0 miles) | Occidental | 31 |
| 1952 | Russ Bonham, Whittier | 21:48 @ Mt. SAC | Whittier | 22 |
| 1951 | John Barnes, Occidental | 22:33 @ Whittier (4.0 miles) | Occidental | 27 |
| 1950 | John Barnes, Occidental | 22:21 @ Tournament Park (4.13 miles) | Occidental | 40 |
| 1949 | John Barnes, Occidental | 22:01 @ Tournament Park (4 miles) | Occidental | 36 |
| 1948 | Edwin Livengood, Redlands | 23:08 @ Caltech (4.0 miles) | Caltech | 31 |
| 1947 | Edwin Livengood, Redlands | 23:33 @ Caltech (4.0 miles) | Redlands | 25 |
| 1946 | Leonard Weed, Redlands | 23:44 @ Tournament Park (4.0 miles) | Redlands | 18 |
| 1945 | no conference meet | (suspended) | no meet | |
| 1944 | Roland Sink, Redlands | 17:32 @ UCLA (3.0 miles) | | ? |
| 1943 | no conference meet | (suspended) | no meet | |
| 1942 | Francis Odell, Caltech | 23:12 @ Tournament Park | Caltech | ? |
| 1941 | Bob Densmore, Caltech | 22:23 @ Rose Bowl (3.95 miles) | Caltech | 21 |
| 1940 | Roy Heaton, Redlands | 22:42 @ Rose Bowl (4.0 miles) | Caltech | 30 |
| 1939 | Roy Heaton, Redlands | 23:23 @ Claremont (4.0 miles) | Pomona | 42 |
| 1938 | Clair Berdel, San Diego | 22:08 @ Claremont (4.0 miles) | San Diego State | ? |
| 1937 | Ernie Viau, San Diego | 21:45 @ Redlands (4.0 miles) | Occidental | 30 |
| 1936 | Dick Brown, Occidental | 22:43 @ Redlands | Redlands | 22 |
| 1935 | Johnny Baker, Whittier | 22:59 @ Occidental (4.0 miles) | Redlands | ? |
| 1934 | Johnny Baker, Whittier | 22:59 @ Whittier (4.0 miles) | Redlands | 28 |
| 1933 | Allen Cole, Redlands | 21:44 @ Rose Bowl Arroyo Seco (4.0 miles) | Redlands | 15 |
| 1932 | Bill Maley, Redlands | 21:06 @ Rose Bowl Arroyo Seco (4.0 miles) | Redlands | 32 |
| 1931 | Folke Skoog, Caltech | 22:26 @ Pomona College (4.0 miles) | Redlands | 26 |
| 1930 | Angus Hull, Redlands | 22:29 @ Claremont | Redlands | ? |
| 1929 | Norman Taylor, Redlands | 20:45 @ Claremont (3.0 miles) | Pomona | 36 |
| 1928 | George White, Pomona | 20:09 @ Ganesha Park | Pomona | 42 |
| 1927 | Linwood Brown, San Diego | 21:42 @ Ganesha Park (4.0 miles) | UCLA | 44 |
| 1926 | Frank Rentschler, Pomona | 20:02 @ Redlands (4.0 miles) | UCLA | 46 |
| 1925 | Edsel Pearcy, UCLA | 22:02 @ Claremont (3.95 miles) | UCLA | 24 |
| 1924 | Kjeld Schmidt, UCLA | 19:45 @ Occidental | Pomona | 31 |
| 1923 | Paul Stroud, Pomona | 19:19 @ Occidental (3.5 miles) | Pomona | 15 |
| 1922 | Lorin Handley, Pomona | 21:39 @ Claremont (3.5 miles) | Pomona | ? |
| 1921 | Hal Sloan, Occidental | 21:15 @ Occidental (3.5 miles) | Occidental | 33 |
| 1920 | Raymond Moreman, Pomona | 16:52 @ Claremont (3.5 miles) | Pomona | 30 |
| 1919 | Sawyer, Redlands | 17:46 | Redlands | 19 |
| 1918 | ? | ? | no record | |
| 1917 | ? | ? | Pomona | 20 |
| 1916 | Ray Adkinson, Pomona | 20:55 @ Eagle Rock | Pomona | 16 |
| 1915 | Ray Adkinson, Pomona | 21:13 @ Pomona College, Claremont - story | Pomona | 15 |