| 1. | 15:44.0 | Ben Tyler | 11 | Shorewood(2-8) | 10/17/2008 | Woodland Conference Meet |
| 2. | 15:48.1 | Michael Stumpf | 12 | Xavier(2-4) | 10/2/2008 | Pulaski Invite |
| 3. | 15:55.1 | Mark Allen | 12 | Port Washington(2-8) | 11/1/2008 | Division 2 State |
| 4. | 15:55.9 | Evan Ross | 12 | Port Washington(2-8) | 11/1/2008 | Division 2 State |
| 5. | 16:04.0 | John Luterbach | 11 | Catholic Memorial(2-7) | 11/1/2008 | Division 2 State |
| 6. | 16:04.5 | Brian Kinnard | 12 | Luxemburg - Casco(2-4) | 11/1/2008 | Division 2 State |
| 7. | 16:05.0 | Aaron Easker | 12 | Wittenberg - Birnamwood(2-2) | 10/2/2008 | Rosholt Invite |
| 8. | 16:06.6 | Bobby Laabs | 12 | Greendale(2-8) | 10/2/2008 | Mukwonago Invite |
| 9. | 16:11.6 | Alec Holguin | 11 | Cudahy(2-8) | 10/17/2008 | Woodland Conference Meet |
| 10. | 16:11.7 | Peter Drews | 11 | Shorewood(2-8) | 10/17/2008 | Woodland Conference Meet |
| 11. | 16:14.8 | Alex Steiner | 12 | Chilton(2-4) | 11/1/2008 | Division 2 State |
| 12. | 16:18.0 | Brett DeNure | 12 | Monroe(2-6) | 10/4/2008 | Platteville Invite |
| 13. | 16:19.8 | Nick VanStrydonk | 12 | Tomahawk(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 14. | 16:21.0 | James Menor | 12 | Peshtigo(2-2) | 10/18/2008 | Peshtigo Invite |
| 15. | 16:22.0 | Tanner Beebe | 11 | Platteville(2-6) | 10/4/2008 | Platteville Invite |
| 16. | 16:23.0 | Patrick Jenkins | 11 | Deerfield - Cambridge(2-7) | 9/30/2008 | Princeton Invite |
| 17. | 16:25.2 | Dayton Lueck | 12 | Wisconsin Lutheran(2-8) | 10/2/2008 | Mukwonago Invite |
| 18. | 16:25.4 | Matt McKenna | 11 | Madison Edgewood(2-6) | 10/4/2008 | Stoughton Invite |
| 19. | 16:26.8 | Maurice McShepard | 12 | Wisconsin Lutheran(2-8) | 10/10/2008 | Wisconsin Lutheran Viking Invite |
| 20. | 16:27.7 | Jessop Keene | 12 | Prescott(2-1) | 11/1/2008 | Division 2 State |
| 21. | 16:29.0 | Zach Zweifel | 12 | Mt. Horeb - Barneveld(2-6) | 10/25/2008 | Division 2 Sectional 6 |
| 22. | 16:32.0 | Lucas Jadin | 12 | Freedom(2-2) | 9/25/2008 | Mishicot Bremser Invite |
| 23. | 16:32.4 | Sam Kitzrow | 11 | Wisconsin Lutheran(2-8) | 10/2/2008 | Mukwonago Invite |
| 24. | 16:33.0 | Bruce Schmitz | 12 | Dodgeville - Mineral Point(2-6) | 10/25/2008 | Division 2 Sectional 6 |
| 25. | 16:34.5 | Evan Lewandowski | 11 | Medford(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 26. | 16:35.0 | Michael Heise | 10 | New London(2-2) | 10/17/2008 | Bay Conference Meet |
| 27. | 16:36.0 | Ben Crawford | 12 | Denmark(2-4) | 10/17/2008 | Bay Conference Meet |
| 28. | 16:36.2 | Jacob Peterson | 11 | Nekoosa - Port Edwards(2-3) | 11/1/2008 | Division 2 State |
| 29. | 16:39.0 | Steve Wagner | 12 | Seymour(2-2) | 8/27/2008 | West De Pere Enduro Meet |
| . | 16:39.0 | Brett Johnson | 10 | St. Croix Central(2-1) | 10/16/2008 | Dunn St. Croix Conference Meet |
| 31. | 16:40.0 | Tony Holzer | 12 | Chilton(2-4) | 9/25/2008 | Mishicot Bremser Invite |
| 32. | 16:41.1 | Cody Lemke | 12 | Tomahawk(2-2) | 10/11/2008 | Tomahawk Invite |
| 33. | 16:43.0 | Dylan Starck | 10 | Monroe(2-6) | 10/4/2008 | Platteville Invite |
| 34. | 16:43.1 | Paul VanGrinsven | 11 | Little Chute(2-4) | 9/5/2008 | Freedom Invite |
| 35. | 16:44.7 | Nathan Kainz | 11 | Tomahawk(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 36. | 16:45.0 | Dan Thompson | 12 | Waupaca(2-2) | 10/18/2008 | Eastern Valley Conference Meet |
| 37. | 16:45.4 | Jake Tsacudakis | 11 | Ripon(2-5) | 9/5/2008 | Freedom Invite |
| 38. | 16:46.3 | Steve Olson | 12 | Delavan - Darien(2-7) | 11/1/2008 | Division 2 State |
| 39. | 16:46.8 | Phil Simac | 12 | Mishicot(2-4) | 9/11/2008 | Cedar Grove Rocket Invite |
| 40. | 16:47.8 | Tyler Willenbrink | 11 | Xavier(2-4) | 11/1/2008 | Division 2 State |
| 41. | 16:48.0 | Sean Wise | 12 | Wautoma(2-5) | 9/18/2008 | Tri-County Invite |
| 42. | 16:48.9 | Andrew Rohlman | 11 | Osceola(2-1) | 11/1/2008 | Division 2 State |
| 43. | 16:49.0 | Cody Kurscheidt | 11 | Chilton(2-4) | 9/25/2008 | Mishicot Bremser Invite |
| 44. | 16:50.0 | Marcus Schickel | 10 | Deerfield - Cambridge(2-7) | 9/30/2008 | Princeton Invite |
| 45. | 16:50.4 | Jeff Condit | 12 | Catholic Memorial(2-7) | 9/27/2008 | Janesville Craig Midwest Invite |
| 46. | 16:50.9 | Jake Wickham | 12 | New Richmond(2-1) | 9/6/2008 | Eau Claire North Husky Invite |
| 47. | 16:51.0 | Sam Arnott | 11 | Tomahawk(2-2) | 10/11/2008 | Tomahawk Invite |
| 48. | 16:51.7 | Jose Perez | 10 | Beloit Turner(2-7) | 9/4/2008 | Cam-Rock Invite |
| 49. | 16:52.7 | Brian Barr | 12 | McFarland(2-6) | 10/4/2008 | Stoughton Invite |
| . | 16:52.7 | Cory Zimmerman | 12 | Adams - Friendship(2-3) | 11/1/2008 | Division 2 State |
| 1. | 16:35.0 | Michael Heise | 10 | New London(2-2) | 10/17/2008 | Bay Conference Meet |
| 2. | 16:39.0 | Brett Johnson | 10 | St. Croix Central(2-1) | 10/16/2008 | Dunn St. Croix Conference Meet |
| 3. | 16:43.0 | Dylan Starck | 10 | Monroe(2-6) | 10/4/2008 | Platteville Invite |
| 4. | 16:50.0 | Marcus Schickel | 10 | Deerfield - Cambridge(2-7) | 9/30/2008 | Princeton Invite |
| 5. | 16:51.7 | Jose Perez | 10 | Beloit Turner(2-7) | 9/4/2008 | Cam-Rock Invite |
| 6. | 16:55.5 | Ben Cipriano | 10 | Whitewater(2-7) | 9/27/2008 | Janesville Craig Midwest Invite |
| 7. | 16:56.0 | Mason Grundy | 10 | Little Chute(2-4) | 10/18/2008 | Eastern Valley Conference Meet |
| 8. | 16:59.0 | Will Peasley | 10 | Black River Falls(2-3) | 9/30/2008 | Sparta Invite |
| 9. | 17:03.9 | Aidan Mazur | 10 | Shorewood(2-8) | 10/17/2008 | Woodland Conference Meet |
| 10. | 17:09.2 | Josh Martin | 10 | Pewaukee(2-7) | 10/17/2008 | Woodland Conference Meet |
| 11. | 17:10.0 | Jon Luedtke | 10 | Lomira(2-5) | 9/12/2008 | Mayville Hurlbert Invite |
| . | 17:10.0 | Ian Cooley | 10 | University School(2-8) | 9/27/2008 | St. Francis Lakeside Invite |
| 13. | 17:14.0 | Wesley Bonack | 10 | Wisconsin Lutheran(2-8) | 10/16/2008 | Wisconsin Little Ten Conference Meet |
| 14. | 17:19.0 | Caden Miller | 10 | Lodi(2-6) | 10/4/2008 | Platteville Invite |
| . | 17:19.0 | David Lund | 10 | Viroqua(2-3) | 10/17/2008 | Coulee Conference Meet |
| 16. | 17:20.0 | Hunter Bloy | 10 | Freedom(2-2) | 10/18/2008 | Eastern Valley Conference Meet |
| 17. | 17:22.0 | Brandon Fraleigh | 10 | New Berlin Eisenhower(2-8) | 10/4/2008 | Eagle Invite |
| 18. | 17:23.0 | Ethan Nault | 10 | Peshtigo(2-2) | 10/18/2008 | Peshtigo Invite |
| . | 17:23.0 | Josh Hoff | 10 | Mt. Horeb - Barneveld(2-6) | 10/25/2008 | Division 2 Sectional 6 |
| 20. | 17:23.2 | Joseph Pendleton | 10 | Shorewood(2-8) | 10/17/2008 | Woodland Conference Meet |
| 21. | 17:24.8 | Chris Rolling | 10 | Thomas More(2-8) | 10/17/2008 | Woodland Conference Meet |
| 22. | 17:25.9 | Joe Luedtke | 10 | Lomira(2-5) | 11/1/2008 | Division 2 State |
| 23. | 17:27.0 | Max Mattei | 10 | Wisconsin Dells(2-3) | 10/18/2008 | South Central Conference Meet |
| 24. | 17:33.6 | Joe Pickett | 10 | Turner(2-7) | 9/27/2008 | Janesville Craig Midwest Invite |
| 25. | 17:33.8 | Max Kelley | 10 | McFarland(2-6) | 10/4/2008 | Stoughton Invite |
| 1. | 17:12.8 | Grey Davis | 9 | Lakeside Lutheran(2-7) | 10/4/2008 | Burlington Chocolate City Invite |
| 2. | 17:13.0 | Brandon Barrette | 9 | Peshtigo(2-2) | 10/18/2008 | Peshtigo Invite |
| 3. | 17:19.0 | Jedd Sebion | 9 | Westby(2-3) | 9/30/2008 | Sparta Invite |
| 4. | 17:25.0 | Hunter Smith | 9 | Nekoosa - Port Edwards(2-3) | 10/18/2008 | South Central Conference Meet |
| 5. | 17:28.0 | Matt Eidenschink | 9 | Nekoosa - Port Edwards(2-3) | 10/18/2008 | South Central Conference Meet |
| 6. | 17:28.2 | Jonathon Melms | 9 | Wisconsin Lutheran(2-8) | 10/2/2008 | Mukwonago Invite |
| 7. | 17:28.3 | Josiah Ricke | 9 | Wisconsin Lutheran(2-8) | 10/2/2008 | Mukwonago Invite |
| 8. | 17:29.0 | Mike Peterson | 9 | Nekoosa - Port Edwards(2-3) | 10/18/2008 | South Central Conference Meet |
| 9. | 17:34.4 | Weston Brusky | 9 | Oconto Falls(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 10. | 17:36.8 | Jed Dodge | 9 | Durand(2-3) | 10/25/2008 | Division 2 Sectional 3 |
| 11. | 17:39.0 | Ryan Zimmerman | 9 | Adams - Friendship(2-3) | 10/18/2008 | South Central Conference Meet |
| 12. | 17:45.0 | Luke Peterson | 9 | Monroe(2-6) | 10/4/2008 | Platteville Invite |
| 13. | 17:45.9 | Devin Bera | 9 | Freedom(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 14. | 17:47.3 | Trevor Faldet | 9 | Port Washington(2-8) | 10/23/2008 | Future Champions @ Menomonee Falls |
| . | 17:47.3 | Keith Dodd | 9 | Shorewood(2-8) | 10/17/2008 | Woodland Conference Meet |
| 16. | 17:52.0 | Jeff Meitler | 9 | Milwaukee Lutheran(2-8) | 10/9/2008 | Port Washington Invite |
| 17. | 17:53.0 | Connor Morovits | 9 | Prairie du Chien(2-6) | 10/4/2008 | Platteville Invite |
| 18. | 17:53.2 | Joel Henry | 9 | Monroe(2-6) | 11/1/2008 | Division 2 State |
| 19. | 18:01.2 | John Vodacek | 9 | Bloomer(2-1) | 10/14/2008 | Heart Of The North Conference Meet |
| 20. | 18:06.2 | Jon Dausey | 9 | Oconto Falls(2-2) | 10/25/2008 | Division 2 Sectional 2 |
| 21. | 18:07.6 | Jordan Daul | 9 | Pewaukee(2-7) | 10/17/2008 | Woodland Conference Meet |
| 22. | 18:12.3 | Joshua Smith | 9 | Ashland(2-1) | 10/24/2008 | Division 2 Sectional 1 |
| 23. | 18:18.6 | Patrick Delaney | 9 | New Berlin West(2-8) | 10/17/2008 | Woodland Conference Meet |
| 24. | 18:20.2 | Joey Ott | 9 | Ripon(2-5) | 11/1/2008 | Division 2 State |
| 25. | 18:21.1 | Josh Patzen | 9 | Union Grove(2-7) | 10/4/2008 | Burlington Chocolate City Invite |