| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | | 12 | Kevin Bennert | 16:12.4 | VA | Woodberry Forest | Sep 18
| Woodberry Forest Invitational |
| 2. | | 11 | Guy Shelby | 16:20.4 | VA | Trinity Episcopal | Oct 2
| Great American Cross Country Festival |
| 3. | | 11 | Ian Granger | 16:26.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 4. | | 11 | Scott Newton | 16:29.4 | VA | Collegiate | Nov 12
| VISAA State Cross Country Championships |
| 5. | | 10 | Mac Strehler | 16:43.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| | | 10 | Reider Strehler | 16:43.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 7. | | 11 | Alden Knipe | 16:52.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 8. | | 12 | Thomas Garrison | 17:02.7PR | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 9. | | 12 | Josh Trudgeon | 17:09.1 | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 10. | | 10 | Grant Wiggins | 17:17.0 | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 11. | | 11 | Chris Cantone | 17:18.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 12. | | 11 | Ben Gross | 17:36.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 13. | | 11 | Addison Winston | 17:39.9 | VA | Woodberry Forest | Oct 9
| Albemarle Invitational |
| 14. | | 10 | Connor Partlow | 17:43.7 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 15. | | 11 | Logan Rafield | 17:46.5 | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 16. | | 12 | Matthew Laws | 17:49.8 | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 17. | | 12 | Michael Paris | 17:53.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 18. | | 12 | Greg Wise | 17:56.0PR | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 19. | | 12 | Farrar Pace | 18:00.0PR | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 20. | | 12 | James Busch | 18:01.0PR | VA | St. Christopher's | Oct 12
| St. Anne's-Belfield Invitational |
| 21. | | 8 | Peter Lomong | 18:06.4 | VA | Fork Union Military Academy | Nov 12
| VISAA State Cross Country Championships |
| 22. | | 10 | Teddy Nasworthy | 18:07.7 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 23. | | 12 | Trip Templeman | 18:08.1 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 24. | | 10 | Jake Wilkes | 18:09.0 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 25. | | 10 | Peter Shelton | 18:09.1 | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 26. | | 10 | Luke Page | 18:09.4 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 27. | | 11 | Thomas Weyrich | 18:17.8PR | VA | Fork Union Military Academy | Oct 9
| Albemarle Invitational |
| 28. | | 11 | Hagood Grantham | 18:20.6 | VA | Woodberry Forest | Oct 9
| Albemarle Invitational |
| 29. | | 10 | Linzy Cumbia | 18:22.0PR | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 30. | | 12 | Nick Richardson | 18:22.7 | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 31. | | 10 | Chris Keeling | 18:23.8PR | VA | St Annes Belfield | Nov 12
| VISAA State Cross Country Championships |
| 32. | | 9 | Joseph Gonnella | 18:24.0PR | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 33. | | 11 | Eddie Whitlock | 18:24.4 | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 34. | | 10 | Rodin Schimper | 18:27.2 | VA | Fork Union Military Academy | Nov 12
| VISAA State Cross Country Championships |
| 35. | | 11 | Nicholas Evans | 18:30.1 | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 36. | | 11 | Ian Rowland | 18:30.8 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 37. | | 12 | Conor Flynn | 18:31.1 | VA | Woodberry Forest | Oct 9
| Albemarle Invitational |
| 38. | | 11 | Jake Levy | 18:37.0PR | VA | Norfolk Academy | Oct 8
| Norfolk Academy Meet #2 |
| 39. | | 12 | William Wilkinson | 18:39.6 | VA | Fork Union Military Academy | Oct 9
| Albemarle Invitational |
| 40. | | 12 | Jamie Ball | 18:41.0 | VA | St. Christopher's | Oct 16
| Fall Classic at Georgetown Prep |
| 41. | | 9 | Tim Viere | 18:42.0 | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 42. | | 12 | Foster Haynes | 18:43.0PR | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 43. | | 10 | Mitchell Phillips | 18:43.8PR | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 44. | | 12 | Jonathan Puwalski | 18:44.7PR | VA | Fork Union Military Academy | Nov 12
| VISAA State Cross Country Championships |
| 45. | | 12 | James Doernberg | 18:45.0 | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 46. | | 10 | Nick Swarup | 18:46.0 | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 47. | | 10 | Alan Salimov | 18:47.0 | VA | Norfolk Academy | Oct 8
| Norfolk Academy Meet #2 |
| 48. | | 12 | Eli Exum | 18:52.7PR | VA | Woodberry Forest | Nov 12
| VISAA State Cross Country Championships |
| 49. | | - | Ryan Puwalski | 18:53.0PR | VA | Fork Union Military Academy | Sep 25
| Maymont XC Festival |
| 50. | | 12 | Stephen Wood | 19:01.0PR | VA | St. Christopher's | Oct 12
| St. Anne's-Belfield Invitational |
| 51. | | 12 | JC Wood | 19:01.6PR | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 52. | | 9 | Reid Barden | 19:06.1 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 53. | | 10 | Jay Windsor | 19:10.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 54. | | 12 | Daniel Duane | 19:17.0 | VA | Norfolk Academy | Oct 8
| Norfolk Academy Meet #2 |
| 55. | | - | Blake Bozymski | 19:18.0PR | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 56. | | 12 | Will Bentley | 19:21.0PR | VA | Fork Union Military Academy | Sep 25
| Maymont XC Festival |
| 57. | | 11 | Jack Gimbert | 19:28.3 | VA | Woodberry Forest | Sep 18
| Woodberry Forest Invitational |
| 58. | | 9 | Alexander Lomong | 19:32.0 | VA | Fork Union Military Academy | Nov 5
| Prep League/LIS XC Championships |
| 59. | | 11 | Drew Rowe | 19:34.2 | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 60. | | 10 | Blake Thatcher | 19:36.0 | VA | St Annes Belfield | Oct 15
| Norfolk Academy Meet #3 |
| 61. | | 11 | Joseph Vandersyde | 19:37.2 | VA | Trinity Episcopal | Nov 12
| VISAA State Cross Country Championships |
| 62. | | 11 | Erwan Mongon | 19:51.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| | | 12 | Brice Bentley | 19:51.0PR | VA | Fork Union Military Academy | Nov 12
| VISAA State Cross Country Championships |
| 64. | | 11 | Danny Murillo | 19:53.0 | VA | St. Christopher's | Oct 16
| Fall Classic at Georgetown Prep |
| 65. | | 9 | Buck Kirtland | 19:55.7 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 66. | | 10 | Will Bruner | 20:01.0 | VA | St. Christopher's | Oct 16
| Fall Classic at Georgetown Prep |
| | | 10 | Will Worsley | 20:01.0 | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 68. | | 9 | Kyle Mosman | 20:12.2 | VA | Collegiate | Nov 12
| VISAA State Cross Country Championships |
| 69. | | 11 | Harrison Ambrosio | 20:13.5PR | VA | Fork Union Military Academy | Nov 12
| VISAA State Cross Country Championships |
| 70. | | 11 | Gregory ScheerCook | 20:14.0 | VA | St. Christopher's | Nov 12
| VISAA State Cross Country Championships |
| 71. | | 10 | Mason Hadley | 20:21.7 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 72. | | 9 | Harrison Geho | 20:27.1PR | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 73. | | 11 | Kyle O'Donnell | 20:28.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 74. | | - | Sabin Jackson | 20:29.0 | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 75. | | 10 | Tom Moss | 20:31.0 | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 76. | | 11 | Timmy McGraw | 20:31.3 | VA | Collegiate | Nov 12
| VISAA State Cross Country Championships |
| 77. | | 10 | Victor Yu | 20:32.0 | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| 78. | | 7 | William Bennett | 20:37.0 | VA | Collegiate | Nov 5
| Prep League/LIS XC Championships |
| 79. | | 11 | Alex Johnson | 20:40.2 | VA | Fork Union Military Academy | Sep 18
| Woodberry Forest Invitational |
| 80. | | 11 | Drew Colletti | 20:52.5 | VA | Collegiate | Nov 12
| VISAA State Cross Country Championships |
| 81. | | 11 | Zach Wiesler | 20:57.7PR | VA | Woodberry Forest | Oct 9
| Albemarle Invitational |
| 82. | | 9 | Adrian Baker | 21:04.0PR | VA | Fork Union Military Academy | Nov 5
| Prep League/LIS XC Championships |
| 83. | | 9 | Nathan Hecht | 21:07.0PR | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| | | 7 | Drew McCory | 21:07.0 | VA | Collegiate | Nov 5
| Prep League/LIS XC Championships |
| 85. | | 10 | Richard Hankins | 21:11.4 | VA | Trinity Episcopal | Oct 16
| Milestat.com Invitational |
| 86. | | 12 | John Charles Wood | 21:15.0PR | VA | Collegiate | Sep 25
| Maymont XC Festival |
| 87. | | 12 | Wyatt Jamerson | 21:20.8PR | VA | Steward | Nov 12
| VISAA State Cross Country Championships |
| 88. | | 11 | Matthew Disler | 21:22.1 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 89. | | 10 | Andrew Hope | 21:24.4PR | VA | Woodberry Forest | Sep 18
| Woodberry Forest Invitational |
| 90. | | - | Trey Bergsma | 21:34.0PR | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 91. | | - | Jordan Buccanich | 21:34.4PR | VA | Fork Union Military Academy | Sep 18
| Woodberry Forest Invitational |
| 92. | | 12 | Chris Davis | 21:40.0 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |
| 93. | | - | Macon Norman | 21:45.9PR | VA | Fork Union Military Academy | Sep 18
| Woodberry Forest Invitational |
| 94. | | 10 | Vernon O'Berry | 21:47.0 | VA | Norfolk Academy | Oct 8
| Norfolk Academy Meet #2 |
| | | - | Andy Han | 21:47.0PR | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 96. | | 10 | Jay Shah | 21:52.0 | VA | Norfolk Academy | Oct 15
| Norfolk Academy Meet #3 |
| | | - | Danny Fisher | 21:52.0PR | VA | Fork Union Military Academy | Nov 5
| Prep League/LIS XC Championships |
| 98. | | 12 | Jimmy Tsai | 21:53.0 | VA | St Annes Belfield | Oct 12
| St. Anne's-Belfield Invitational |
| 99. | | 11 | Frankie Pruitt | 21:54.0 | VA | Woodberry Forest | Nov 5
| Prep League/LIS XC Championships |
| 100. | | 10 | Nate Largo | 21:54.4 | VA | Collegiate | Oct 20
| Collegiate, Patrick Henry at Mills E Godwin |