| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | | 12 | Bobby Peavey | 15:00.0PR | VA | Floyd E Kellam | Sep 20
| William & Mary Invitational |
| 2. | | 12 | Thomas Porter | 15:01.0PR | VA | Mountain View | Nov 29
| Foot Locker South Regional |
| 3. | | 12 | Leoule Degfae | 15:04.0PR | VA | Thomas A Edison | Nov 29
| Foot Locker South Regional |
| 4. | | 12 | Ben Dejarnette | 15:04.9PR | VA | Atlee | Oct 18
| Fall Classic |
| 5. | | 11 | Blake Theroux | 15:08.0PR | VA | Western Branch | Sep 20
| William & Mary Invitational |
| 6. | | 12 | Scott Plunkett | 15:34.3PR | VA | Annandale | Oct 18
| Fall Classic |
| 7. | | 11 | Ted Richardson | 15:38.0 | VA | James River (Midlothian) | Nov 29
| Foot Locker South Regional |
| 8. | | 12 | Chris Werner | 15:43.0PR | | UNAT-VA | Nov 29
| Foot Locker South Regional |
| 9. | | 11 | Anthony Kostelac | 15:44.0PR | VA | Albemarle | Nov 29
| Nike Cross Southeast Regionals (NXN) |
| 10. | | 12 | Luke Noble | 15:47.0PR | VA | Albemarle | Nov 29
| Nike Cross Southeast Regionals (NXN) |
| 11. | | 12 | Jared Berman | 15:51.0PR | VA | James Robinson | Oct 11
| Glory Days Invitational |
| | | 11 | Christopher Foley | 15:51.0PR | | UNAT-VA | Nov 29
| Foot Locker South Regional |
| 13. | | 11 | Andrew McCullen | 15:55.0 | VA | Oakton | Nov 8
| VHSL State Cross Country Championships |
| | | 11 | Drew Paisley | 15:55.0 | VA | Ocean Lakes | Nov 8
| VHSL State Cross Country Championships |
| 15. | | 12 | Griffith Ashooh | 15:58.0PR | VA | Colonial Forge | Nov 8
| VHSL State Cross Country Championships |
| 16. | | 12 | Tihut Degfae | 15:59.0 | VA | Thomas A Edison | Nov 8
| VHSL State Cross Country Championships |
| 17. | | 11 | Brandyn Dyke | 16:01.0PR | VA | Menchville | Sep 17
| Menchville @ Woodside |
| 18. | | 12 | Neal Hendricks | 16:03.0 | VA | Oakton | Oct 4
| Wendy's Invitational 2008 |
| 19. | | 12 | Griff Ashooh | 16:04.0PR | VA | Colonial Forge | Sep 20
| William & Mary Invitational |
| 20. | | 11 | Patrick Fulghum | 16:05.0 | VA | Oakton | Oct 4
| Wendy's Invitational 2008 |
| 21. | | 12 | Stuart Steen | 16:06.0PR | VA | James Robinson | Oct 11
| Glory Days Invitational |
| 22. | | 11 | Jordan White | 16:08.0 | VA | Great Bridge | Nov 8
| VHSL State Cross Country Championships |
| 23. | | 12 | Brett Mandeville | 16:10.0PR | VA | South County | Oct 11
| Glory Days Invitational |
| 24. | | 10 | Graham Wilson | 16:12.0PR | VA | Menchville | Sep 17
| Menchville @ Woodside |
| | | 11 | George Matais | 16:12.0 | VA | Western Branch | Sep 20
| William & Mary Invitational |
| 26. | | 10 | Andy Hesse | 16:14.3PR | VA | Atlee | Oct 18
| Fall Classic |
| 27. | | 11 | Kyle Corwin | 16:15.0PR | VA | Hickory | Sep 20
| William & Mary Invitational |
| | | 12 | Chris Weil | 16:15.0PR | VA | Oakton | Oct 4
| Wendy's Invitational 2008 |
| | | 12 | Alec Ward | 16:15.0PR | VA | Douglas Freeman | Nov 8
| VHSL State Cross Country Championships |
| | | 11 | Brian Davenport | 16:15.0 | VA | Abraham Baldwin (Ga.) | Nov 8
| VHSL State Cross Country Championships |
| 31. | | 10 | Andrew Catanese | 16:16.5 | VA | Atlee | Oct 18
| Fall Classic |
| 32. | | 12 | Booth Hornsby | 16:18.0PR | VA | Deep Run | Sep 24
| Deep Run, Douglas Freeman, John Marshall |
| 33. | | 11 | Andrew Paisley | 16:18.2PR | VA | Ocean Lakes | Sep 17
| Virginia Beach Schools Meet #2 |
| 34. | | 12 | Roger Cooke | 16:19.0PR | VA | Hermitage | Sep 24
| Hermitage, Collegiate, Mills Godwin |
| 35. | | 11 | Kyle Jacobs | 16:20.0 | VA | Western Branch | Sep 20
| William & Mary Invitational |
| | | 12 | Dan Grimm | 16:20.0PR | VA | Centreville | Oct 11
| Glory Days Invitational |
| | | 12 | Daniel Pelletier | 16:20.0PR | VA | North Stafford | Nov 8
| VHSL State Cross Country Championships |
| 38. | | 11 | Michael Ejigu | 16:20.3PR | VA | Annandale | Oct 18
| Fall Classic |
| 39. | | 11 | Wes Steenburgh | 16:21.2PR | VA | Atlee | Oct 18
| Fall Classic |
| 40. | | 12 | Conor Doan | 16:21.6PR | VA | Ocean Lakes | Sep 17
| Virginia Beach Schools Meet #2 |
| 41. | | 12 | Ethan Katz | 16:22.0PR | VA | W T Woodson | Sep 20
| William & Mary Invitational |
| | | 10 | Talbot Armstrong | 16:22.0PR | VA | Fauquier | Nov 8
| VHSL State Cross Country Championships |
| 43. | | 12 | Eric Flanagan | 16:24.0PR | VA | James Robinson | Oct 11
| Glory Days Invitational |
| 44. | | 10 | Silas Frantz | 16:25.0 | VA | Douglas Freeman | Sep 24
| Deep Run, Douglas Freeman, John Marshall |
| 45. | | 12 | Cameron Keys | 16:28.0PR | VA | W T Woodson | Sep 20
| William & Mary Invitational |
| | | 12 | Alex Miller | 16:28.0PR | VA | W T Woodson | Sep 20
| William & Mary Invitational |
| | | 12 | Todd Van Luling | 16:28.0PR | VA | Herndon | Nov 8
| VHSL State Cross Country Championships |
| 48. | | 12 | Nathan Rouse | 16:29.0PR | VA | Albemarle | Nov 29
| Nike Cross Southeast Regionals (NXN) |
| 49. | | 12 | Peter Askin | 16:30.0PR | VA | Maggie L. Walker | Sep 13
| Newport News Invitational |
| | | 11 | Aaron Harrison | 16:30.0 | VA | Grassfield | Sep 20
| William & Mary Invitational |
| | | 12 | Seth Cunningham | 16:30.0 | VA | Ocean Lakes | Nov 8
| VHSL State Cross Country Championships |
| 52. | | 11 | Taylor Torino | 16:31.0 | VA | Colonial Forge | Sep 20
| William & Mary Invitational |
| | | 11 | Yazid Zouaimia | 16:31.0 | VA | Centreville | Oct 11
| Glory Days Invitational |
| | | 11 | Tom Keefe | 16:31.0PR | VA | South County | Oct 11
| Glory Days Invitational |
| | | 12 | Garrett Bradley | 16:31.0PR | VA | Albemarle | Nov 29
| Nike Cross Southeast Regionals (NXN) |
| 56. | | 10 | William Sickenberge... | 16:31.6 | VA | South Lakes | Oct 4
| Frank Keyser Invitational |
| 57. | | 12 | Alex Witko | 16:33.0 | VA | Thomas Jefferson S&T | Oct 11
| Glory Days Invitational |
| 58. | | 10 | Nicholas Guarnaccia | 16:33.5 | VA | South Lakes | Oct 4
| Frank Keyser Invitational |
| 59. | | 10 | Nick Reed | 16:35.0 | VA | James Robinson | Oct 11
| Glory Days Invitational |
| | | 12 | Kyle Ward | 16:35.0PR | VA | Douglas Freeman | Nov 8
| VHSL State Cross Country Championships |
| 61. | | 12 | Spencer Rodriguez | 16:36.0PR | VA | Thomas A Edison | Sep 20
| William & Mary Invitational |
| | | 12 | Devin Lacks | 16:36.0PR | VA | Varina | Sep 20
| William & Mary Invitational |
| 63. | | 12 | Justin Kendall | 16:38.0PR | VA | Lloyd C Bird | Sep 17
| L.C. Bird, Clover Hill, George Wythe |
| | | 11 | Lawrence Thomas | 16:38.0 | VA | Landstown | Sep 20
| William & Mary Invitational |
| | | 9 | Shaquon Wilkins | 16:38.0 | VA | Riverbend | Nov 8
| VHSL State Cross Country Championships |
| | | 12 | Greg Kaczka | 16:38.0PR | VA | Deep Run | Nov 29
| Foot Locker South Regional |
| 67. | | 11 | Will McPherson | 16:39.0 | VA | Douglas Freeman | Sep 24
| Deep Run, Douglas Freeman, John Marshall |
| | | 12 | Karlan Cruz | 16:39.0PR | VA | Oakton | Nov 8
| VHSL State Cross Country Championships |
| | | 12 | Colin Maloney | 16:39.0PR | VA | Thomas Jefferson S&T | Nov 8
| VHSL State Cross Country Championships |
| 70. | | 11 | Jack Jasper | 16:39.1 | VA | Herndon | Sep 6
| Fork Union Invitational |
| 71. | | 10 | Jeremy Greenwald | 16:40.0 | VA | Grassfield | Sep 20
| William & Mary Invitational |
| 72. | | 11 | Tyler Iwanicki | 16:41.0PR | VA | Forest Park | Sep 20
| William & Mary Invitational |
| | | 12 | Nolan Compton | 16:41.0PR | VA | Osbourn Park | Nov 8
| VHSL State Cross Country Championships |
| | | 11 | Alex Clark | 16:41.0 | VA | Lake Braddock Secondary | Nov 8
| VHSL State Cross Country Championships |
| 75. | | 11 | Matt Woodhouse | 16:42.0 | VA | Oakton | Oct 4
| Wendy's Invitational 2008 |
| | | 12 | Eric Williamson | 16:42.0PR | VA | Thomas Dale | Nov 1
| VHSL Central Region Championships |
| | | 12 | Timmy Galvin | 16:42.0PR | VA | Thomas Jefferson S&T | Nov 8
| VHSL State Cross Country Championships |
| | | 11 | Bradley Shultis | 16:42.0 | VA | Mountain View | Nov 8
| VHSL State Cross Country Championships |
| | | 12 | John Cruz | 16:42.0PR | VA | Lake Braddock Secondary | Nov 8
| VHSL State Cross Country Championships |
| 80. | | 11 | Joseph Daversa | 16:43.0 | VA | Grassfield | Sep 20
| William & Mary Invitational |
| | | 10 | Cody Snyder | 16:43.0 | VA | Mechanicsville | Sep 20
| Oatlands Invitational |
| | | 12 | Jack D Canatsey | 16:43.0PR | VA | Westfield | Oct 11
| Glory Days Invitational |
| | | 12 | Daniel Tobin | 16:43.0PR | VA | West Springfield | Nov 8
| VHSL State Cross Country Championships |
| 84. | | 11 | Joshua Chartier | 16:44.0PR | VA | W T Woodson | Sep 20
| William & Mary Invitational |
| | | 11 | Mattson Heiner | 16:44.0PR | VA | Centreville | Oct 11
| Glory Days Invitational |
| 86. | | 12 | Alexander Witko | 16:45.0PR | VA | Thomas Jefferson S&T | Nov 8
| VHSL State Cross Country Championships |
| | | 12 | Dante Morales | 16:45.0PR | VA | Oakton | Nov 8
| VHSL State Cross Country Championships |
| 88. | | 12 | Phil Blankenship | 16:46.0PR | VA | Kempsville | Sep 20
| William & Mary Invitational |
| | | 11 | Steven Zaboji | 16:46.0PR | VA | South Lakes | Oct 4
| Frank Keyser Invitational |
| | | 11 | David Gerlach | 16:46.0 | VA | Menchville | Oct 11
| Glory Days Invitational |
| 91. | | 11 | Joey Jachowski | 16:48.0PR | VA | Thomas Jefferson S&T | Oct 11
| Glory Days Invitational |
| | | 11 | Steve San Miguel | 16:48.0PR | VA | Washington-Liberty | Oct 11
| Glory Days Invitational |
| | | 11 | Logan O'Baker | 16:48.0 | VA | Mountain View | Nov 8
| VHSL State Cross Country Championships |
| 94. | | 10 | Evan Niciphor | 16:48.2 | VA | Cosby | Sep 17
| Monacan, Cosby, Manchester |
| 95. | | 11 | Christian Sierra | 16:50.0PR | VA | Western Branch | Sep 20
| William & Mary Invitational |
| | | 11 | Dupree Bostic | 16:50.0PR | VA | Hermitage | Nov 1
| VHSL Central Region Championships |
| | | 10 | Luke Sohl | 16:50.0 | VA | Lake Braddock Secondary | Nov 8
| VHSL State Cross Country Championships |
| | | 12 | Zachary Vrhovac | 16:50.0PR | VA | Albemarle | Nov 29
| Nike Cross Southeast Regionals (NXN) |
| 99. | | 12 | Jason Thorpe | 16:50.2PR | VA | Manchester | Sep 17
| Monacan, Cosby, Manchester |
| 100. | | 11 | Nick Clark | 16:51.0PR | VA | Hermitage | Nov 8
| VHSL State Cross Country Championships |
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