TRL District
| Year | Team Champion | Pts | Runnerup | Pts | Individual | Team | Time |
| 1983 | Lake Oswego | 32 | West Linn | 52 | Lou Lauman | West Linn | 15:38 |
| 1984 | Clackamas | 53 | West Linn | 67 | Doug Henderson | Lake Oswego | 15:34 |
| 1985 | Oregon City | 36 | Clackamas | 42 | Chuck Jewell | Clackamas | 16:09 |
| 1986 | Canby | 54 | Lakeridge | 58 | Mark Weber | Canby | 15:24 |
| 1987 | Lakeridge | 55 | Milwaukie | 80 | Bill Shaw | Oregon City | 15:26 |
| 1988 | West Linn | 52 | Rex Putnam | 55 | Kevin Buse | West Linn | 16:02 |
| 1989 | Lakeridge | 56 | Rex Putnam | 78 | Mike Mahoney | West Linn | 16:00 |
| 1990 | Canby | 44 | Lake Oswego | 49 | Tracy Hollister | Lake Oswego | 15:41 |
| 1991 | Canby | 43 | Lakeridge | 79 | Brendan Hughes | Lakeridge | 15:48 |
| 1992 | Canby | 45 | West Linn | 62 | Dan Browne | West Linn | 15:20 |
| 1993 | West Linn | 40 | Oregon City | 55 | Ryan Burke | West Linn | 15:48 |
| 1994 | Oregon City | 41 | West Linn | 41 | Matt Johnson | Oregon City | 15:56 |
| 1995 | Oregon City | 26 | Lakeridge | 71 | Matt Johnson | Oregon City | 15:59 |
| 1996 | Oregon City | 15 | West Linn | 87 | Matt Johnson | Oregon City | 15:43 |
| 1997 | Clackamas | 44 | Oregon City | 71 | Kyle Barker | Oregon City | 16:05 |
| 1998 | Oregon City | 49 | West Linn | 67 | Josh Monroe | Milwaukie | 15:46 |
| 1999 | Oregon City | 32 | Rex Putnam | 62 | Kalen Abbot | Oregon City | 16:00 |
| 2000 | Rex Putnam | 69 | Oregon City | 69 | Kalen Abbot | Oregon City | 15:24 |
| 2001 | Lake Oswego | 50 | Rex Putnam | 63 | Jake Laminack | Rex Putnam | 16:00 |
| 2002 | Rex Putnam | 50 | Lake Oswego | 83 | Jordan Pommerening | Rex Putnam | 16:32 |
| 2003 | Clackamas | 54 | Rex Putnam | 55 | Jordan Pommerening | Rex Putnam | 15:55 |
| 2004 | St. Helens | 56 | Lake Oswego | 62 | Brandon Snook | Oregon City | 16:31 |
| 2005 | St. Helens | 35 | Clackamas | 43 | Ben Frisbee | Lake Oswego | 16:05 |
| 2006 | Clackamas | 42 | Lakeridge | 62 | Riley Werner | Lake Oswego | 16:06 |
| 2007 | Clackamas | 51 | West Linn* Lake Oswego |
61 | Dave Marks | Lakeridge | 16:03 |
| 2008 | West Linn | 41 | Lake Oswego | 49 | Elijah Greer | Lake Oswego | 15:52 |
| 2009 | West Linn | Lakeridge | Cullen Wannarka | West Linn | 16:17 |
| Year | Champion | Pts | Runnerup | Pts | Invividual | School | Time |
| 1983 | Rex Putnam | 36 | Lakeridge | 38 | Pat Monnie | Lakeridge | 10:43 |
| 1984 | Lakeridge | 26 | Oregon City | 50 | Kelly Thalman | West Linn | 10:59 |
| 1985 | Lakeridge | 43 | West Linn | 61 | Kelly Thalman | West Linn | 10:59 |
| 1986 | Lakeridge | 31 | West Linn | 63 | Stacy Hughes | Lakeridge | 10:50 |
| 1987 | Lakeridge | 46 | West Linn | 51 | Aimee Edwards | Lakeridge | 11:08 |
| 1988 | West Linn | 56 | Milwaukie | 60 | Nicole Woodward | West Linn | 10:38 |
| 1989 | Lakeridge | 57 | West Linn | 61 | Tara Loiodici | Oregon City | 11:04 |
| 1990 | West Linn | 38 | Lake Oswego | 45 | Annemarie Southwell | Lake Oswego | 11:27 |
| 1991 | West Linn | 37 | Lake Oswego | 49 | DeAnne Keller | West Linn | 11:00 |
| 1992 | Tualatin | 52 | Clackamas | 53 | Katrina deBoer | West Linn | 10:43 |
| 1993 | Clackamas | 46 | West Linn | 53 | Jamie Fairchild | Tualatin | 18:41 |
| 1994 | West Linn | 39 | Oregon City | 58 | Katrina deBoer | West Linn | 19:05 |
| 1995 | Oregon City | 39 | West Linn | 47 | Sara Barker | Oregon City | 19:09 |
| 1996 | West Linn | 41 | Lakeridge | 63 | Jill Rencher | West Linn | 18:41 |
| 1997 | Oregon City | 26 | West Linn | 74 | Miranda Vorres | Oregon City | 19:08 |
| 1998 | Oregon City | 36 | West Linn | 59 | April Fitzgerald | Oregon City | 18:36 |
| 1999 | Oregon City | 28 | Rex Putnam | 63 | April Fitzgerald | Oregon City | 19:03 |
| 2000 | Oregon City | 47 | Lakeridge | 67 | Shawn Kelly | Lake Oswego | 18:36 |
| 2001 | Lakeridge | 58 | West Linn | 59 | Emily Wilson | Lakeridge | 18:51 |
| 2002 | West Linn | 57 | Lake Oswego | 67 | Berkeley Aldinger-Gibson | Lakeridge | 18:55 |
| 2003 | Lake Oswego | 41 | Clackamas | 50 | Claire Michel | Clackamas | 18:23 |
| 2004 | Clackamas | 48 | Lake Oswego | 52 | Claire Michel | Clackamas | 18:55 |
| 2005 | West Linn | 37 | Clackamas | 44 | Claire Michel | Clackamas | 18:21 |
| 2006 | West Linn | 56 | Clackamas | 61 | Claire Michel | Clackamas | 18:18 |
| 2007 | West Linn | 50 | Lake Oswego | 51 | Tate Murray | Lake Oswego | 19:13 |
| 2008 | West Linn | 34 | Lake Oswego | 71 | Tate Murray | Lake Oswego | 18:44 |
| 2009 | West Linn | 64 | Lake Oswego | 69 | Tate Murray | Lake Oswego | 18:33 |
