| 2024 | Jase Burton | Star Valley | 15:46.6 | Trajn Swalstad | Worland | 16:08.0 | Jadeth Elder | Thermopolis | 17:43.8 | at Cheyenne Country Club |
| 2023 | Habtamu Wetzel | Star Valley | 15:48.30 | Charlie Hulbert | Cody | 16:10.20 | Howard McNiven | Burlington | 17:40.40 | at Cheyenne Country Club |
| 2022 | Habtamu Wetzel | Star Valley | 15:48.04 | Owen Burnett | Mountain View | 16:04.37 | Grant Bartlett | Saratoga | 17:24.58 | at Ethete |
| 2021 | Mason Wheeler | Jackson | 16:10.45 | Owen Burnett | Mountain View | 16:16.47 | Grant Bartlett | Saratoga | 17:01.83 | at Ethete |
| 2020 | Ben Williams | Jackson | 15:55.16 | Peter Visser | Star Valley | 15:48.8 | Grant Bartlett | Saratoga | 18:33.49 | 4A at Casper, Paradise Valley CC; 3A at Afton, Valleyvue GC; 2A at Douglas Country Club |
| 2019 | Trevor Stephen | Cheyenne Central | 16:26.9 | Peter Visser | Star Valley | 16:01.26 | Grant Bartlett | Saratoga | 17:04.58 | at Afton, Valleyvue GC |
| 2018 | Weston Wiley | Evanston | 16:03.74 | Peter Visser | Star Valley | 15:56.21 | Jarom Herring | Saratoga | 17:29.77 | at Sheridan, VA |
| 2017 | Albert Steiner | Laramie | 15:55.06 | Asefa Wetzel | Star Valley | 16:28.38 | Jarom Herring | Saratoga | 17:50.12 | at Sheridan, VA |
| 2016 | Philip Henry | Laramie | 15:52.05 | Shane Henderson | Star Valley | 16:00.39 | Reid Schroeder | Saratoga-Encampment | 17:39.69 | at Sheridan, VA |
| 2015 | Chris Henry | Laramie | 15:29.39 | Brody Smith | Cody | 15:23.33 | Jorge Garcia | Burns-Pine Bluffs | 16:48.68 | at Sheridan, VA |
| 2014 | Chris Henry | Laramie | 15:33.79 | Brody Smith | Cody | 15:45.50 | Keegan Her Many Horses | Wyoming Indian | 17:28.26 | at Sheridan, VA |
| 2013 | Jonah Henry | Laramie | 15:22.32 | Cody Peck | Star Valley | 15:56.90 | Wilson Clifford | Wyoming Indian | 17:12.12 | at Sheridan, VA |
| 2012 | Ricky Faure | Rock Springs | 16:33.78 | Devyn Brotherton | Cody | 17:13.82 | Wilson Clifford | Wyoming Indian | 17:43.37 | at Douglas Country Club |
| 2011 | Ricky Faure | Rock Springs | 16:43.91 | Oliver Scofield | Jackson | 16:51.68 | Alejandro Garcia | Burns-Pine Bluffs | 17:41.03 | at Douglas Country Club |
| 2010 | Alex Sorensen | Evanston | 16:20.66 | Oliver Scofield | Jackson | 17:09.08 | Colin May | Lovell | 18:03.36 | at Douglas Country Club |
| 2009 | Spencer Pecha | Campbell County | 16:16.48 | Andy Phillips | Jackson | 16:56.86 | Caleb Her Many Horses | Wyoming Indian | 16:36.52 | at Sheridan, VA |
| 2008 | Dominick Robinson | Campbell County | 16:15.35 | Andy Phillips | Jackson | 17:19.51 | Caleb Her Many Horses | Wyoming Indian | 16:50.36 | at Sheridan, VA |
| 2007 | Dominick Robinson | Campbell County | 16:28.5 | Brock Rose | Newcastle | 17:30.6 | Caleb Her Many Horses | Wyoming Indian | 17:30.9 | at Douglas Country Club |
| 2006 | Paul Burke | Campbell County | 16:06.38 | Brock Rose | Newcastle | 17:32.54 | Hayden Hohnholt | Saratoga | 17:41.14 | at Cheyenne, Prairie View GC |
| 2005 | Zac Reiter | Rock Springs | 16:09 | Toby Patterson | Douglas | 17:32 | Riley Tall Whiteman | Wyoming Indian | 17:38 | at Cheyenne, Prairie View GC |
| 2004 | Graydon Curry | Campbell County | 16:28.8 | Matt Heller | Lander | 16:24.1 | Brett Schuler | Wright | 17:00.0 | at Worland, Green Hills GC |
| 2003 | Cole Weaver | Campbell County | 16:27.5 | Matt Heller | Lander | 16:27.7 | Brett Schuler | Wright | 17:11.9 | at Douglas Country Club |
| 2002 | Andrew Jones | Campbell County | 15:54.8 | Matt Heller | Lander | 16:39.3 | Brett Schuler | Wright | 17:03.1 | at Riverton, Renegade GC |
| 2001 | Tony Bachman | Campbell County | 16:18.33 | Beau Baldock | Jackson | 17:03.48 | Mark Pieper | Sundance | 17:07.57 | at Douglas Country Club |
| 2000 | Tony Bachman | Campbell County | 16:16.16 | Arte Huhn | Jackson | 16:38.82 | Mark Pieper | Sundance | 16:52.57 | at Riverton, Renegade GC |
| 1999 | Tim Williams | Laramie | 16:19 | Shane Shatto | Douglas | 16:48 | Jason Taylor | Snake River | 16:53 | at Cheyenne, Prairie View GC |
| 1998 | Morgan McLeland | Campbell County | 16:23.94 | John Beck | Torrington | 17:19.69 | Beaver C'Bearing | Wyoming Indian | 18:19.75 | at Douglas Country Club |
| 1997 | Jered Harns | Rock Springs | 16:22 | Rob Marney | Torrington | 16:46 | Luke Brown | Wyoming Indian | 17:13 | at Riverton Country Club |
| 1996 | Paul Rigsby | Campbell County | 16:31.7 | Rob Marney | Torrington | 17:10.6 | Mike Jesperson | Moorcroft | 16:58.4 | at Douglas Country Club |
| 1995 | Joe Dunham | Laramie | 16:17.53 | Rob Marney | Torrington | 16:45.75 | Norman Vigil | Snake River | 17:03.65 | at Riverton Country Club |
| 1994 | Erik Kean | Cheyenne Central | 16:27.66 | Mick Parsons | Newcastle | 17:07.66 | Norman Vigil | Snake River | 17:53.17 | at Douglas Country Club |
| 1993 | Jeremy Skinner | Campbell County | 16:05.82 | Joe Wilson | Torrington | 16:48.70 | Kyle Raab | Wright | 18:00.78 | at Riverton Country Club |
| 1992 | Mike Wilkey | Green River | 16:17.6 | Ben Sandy | Newcastle | 16:59.8 | Sterling Howell | Wyoming Indian | 17:28.4 | at Cheyenne, Little America GC |
| 1991 | Mike Wilkey | Green River | 16:42 | Tawn Gopp | Worland | 17:06 | - | - | - | at Gillette, CamPlex Park |
| 1990 | Jim McCreery | Campbell County | 16:48 | Jason Bussey | Glenrock | 17:31 | - | - | - | at Lander Golf and Country Club |
| 1989 | Jim McCreery | Campbell County | 16:38 | Mike Makeshine | St. Stephens | 17:21 | - | - | - | at Douglas Country Club |
| 1988 | Jason Drake | Campbell County | 15:51 | - | - | - | Jay Sutherland | Wright | 16:55 | at Worland Municipal Golf Course |
| 1987 | Mike Rickard | Natrona | 16:26 | - | - | - | Jay Sutherland | Wright | 17:30 | at Riverton Country Club |
| 1986 | Mike Thomas | Jackson | 17:55 | - | - | - | Trevor Kaisler | Snake River | 18:40 | at Glenrock, Indian Hills GC |
| 1985 | Jim Williams | Glenrock | 17:33 | - | - | - | Trevor Kaisler | Snake River | 18:55 | at Sheridan, Kendrick GC |
| 1984 | Ron Poe | Kelly Walsh | 15:45 | - | - | - | Trevor Kaisler | Snake River | 17:10 | at Worland |
| 1983 | Jody Fischer | Campbell County | 13:10.23 | - | - | - | Joe Alvarez | Snake River | 14:11.85 | at Cheyenne, Prairie View GC |
| 1982 | Jody Fischer | Campbell County | 13:07.8 | - | - | - | Joe Alvarez | Snake River | 14:39.9 | at Douglas Country Club |
| 1981 | Fred Devore | Natrona | 13:08 | - | - | - | Terry Dick | Snake River | 14:44 | at Lander, American Legion GC |
| 1980 | Brian Clark | Cheyenne East | 12:43 | - | - | - | Rick Hatcher | Burns | 13:33 | at Casper Municipal GC |
| 1979 | Dean Mahaffey | Natrona | 13:52 | - | - | - | Bill Blackburn | Snake River | 15:44 | at Casper Municipal GC |
| 1978 | Kurt Davis | Cheyenne East | 12:49 | - | - | - | Ray Mutz | Rock River | 14:17 | at Worland GC |
| 1977 | Kurt Davis | Cheyenne East | 12:55 | - | - | - | Truit Trowbridge | Encampment | 13:48 | at Cheyenne, Prairie View GC |
| 1976 | Mark Charkey | Cheyenne Central | 13:28 | - | - | - | Dave McWilliams | Burns | 13:01 | at Lander |
| 1975 | Rick Bishop | Cheyenne East | 11:44 | - | - | - | Gabriel Ruiz | LaGrange | 13:29 | at Casper Municipal GC |
| 1974 | Ed Bundy | Cheyenne Central | 9:35 | - | - | - | Jerry Smith | Encampment | 10:35 | at Cheyenne, Little America GC |
| 1973 | Steve Allen | Cheyenne Central | 10:49 | - | - | - | Jerry Smith | Encampment | 11:54 | at Worland |
| 1972 | Steve Allen | Cheyenne Central | 11:57 | - | - | - | Rod Schuppan | LaGrange | 13:07 | at Casper, Paradise Valley CC |
| 1971 | Steve Allen | Cheyenne Central | 11:34.1 | - | - | - | Arnold Alire | LaGrange | 11:47.9 | at Lander |
| 1970 | David Lind | Cheyenne Central | 12:16 | - | - | - | Dan Thomas | Burlington | 12:28 | at Worland |
| 1969 | Tom Takach | Sheridan | 10:29.4 | - | - | - | Jan Buckmaster | Wind River | 10:56.5 | at Riverton |
| 1968 | Kit Carpenter | Cheyenne Central | 10:05.3 | - | - | - | Mike Yates | LaGrange | 10:50.0 | at Lander |
| 1967 | Kit Carpenter | Cheyenne Central | 11:11.1 | - | - | - | Mike Yates | LaGrange | 12:09 | at Laramie |
| 1966 | Louis Maestas | Cheyenne Central | 8:45.1 | - | - | - | Bob Wood | Ten Sleep | 8:53.3 | at Laramie |
| 1965 | Nelson Moss | Lander | 10:34.5 | - | - | - | Bob Wood | Ten Sleep | 11:00 | at Laramie |
| 1964 | Ron Ortiz | Cheyenne East | 10:41.5 | - | - | - | Dick Esquibel | Fort Laramie | 12:01.7 | at Laramie |
| 1963 | Bob Reese | Natrona | 11:24 | - | - | - | Dennis Thales | LaGrange | 12:25.5 | at Laramie |