| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | | 12 | Tyler Spear | 15:07.9PR | MD | Loyola Blakefield | Nov 30
| Nike Southeast Regional (NXN) |
| 2. | 17 | 12 | Collin Crilly | 15:36.0 | MD | Our Lady Of Good Counsel | Sep 28
| Carlisle Invitational |
| 3. | | 11 | Michael Singer | 15:50.0 | MD | McDonogh | Sep 28
| Barnhart Invitational |
| 4. | | 12 | Tyler Richards | 15:59.0PR | MD | Our Lady Of Good Counsel | Sep 28
| Carlisle Invitational |
| 5. | | 11 | Michael Wegner | 16:16.9 | MD | Loyola Blakefield | Nov 30
| Nike Southeast Regional (NXN) |
| 6. | | 12 | Dominic Genuario | 16:18.7PR | MD | Mount Saint Joseph | Nov 6
| MIAA Championships |
| 7. | | 12 | Jack Hamed | 16:22.5PR | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 8. | | 12 | Alex Armbruster | 16:28.0PR | MD | St. Andrew's Episcopal | Sep 21
| Mercersburg Invitational |
| 9. | | 10 | Frankie Legambi | 16:30.0 | MD | Loyola Blakefield | Sep 28
| Barnhart Invitational |
| 10. | | 10 | Kevin Wegner | 16:32.8 | MD | Loyola Blakefield | Nov 6
| MIAA Championships |
| 11. | | 11 | Owen Budd | 16:35.4PR | MD | Calvert Hall College | Nov 6
| MIAA Championships |
| 12. | | 11 | Andrew Michelson | 16:38.0 | MD | McDonogh | Sep 28
| Barnhart Invitational |
| 13. | | 10 | Kevin McGivern | 16:39.6 | MD | Our Lady Of Good Counsel | Nov 30
| Nike Southeast Regional (NXN) |
| 14. | | 10 | Jack Wavering | 16:39.8 | MD | Our Lady Of Good Counsel | Nov 30
| Nike Southeast Regional (NXN) |
| 15. | | 12 | Patrick Dunk | 16:47.0PR | MD | Calvert Hall College | Sep 21
| 62nd Annual Spiked Shoe Invitational |
| 16. | | 11 | John Podles | 16:49.0 | MD | Calvert Hall College | Sep 21
| 62nd Annual Spiked Shoe Invitational |
| 17. | | 11 | Ronan O'Shea | 16:50.5 | MD | Archbishop Spalding | Nov 6
| MIAA Championships |
| 18. | 17 | 11 | Joe Graham | 16:55.2PR | MD | DeMatha Catholic | Sep 21
| Adidas Cross Country Challenge |
| 19. | | 12 | Joey Pickens | 16:57.6PR | MD | Glenelg Country | Nov 6
| MIAA Championships |
| 20. | | 10 | Evan Moore | 16:58.6 | MD | John Carroll | Nov 6
| MIAA Championships |
| 21. | 16 | 10 | Jeff Moxley | 16:58.8PR | MD | Our Lady Of Good Counsel | Nov 30
| Nike Southeast Regional (NXN) |
| 22. | | 12 | Will Hopkins | 16:59.0PR | MD | John Carroll | Nov 9
| Maryland and DC Private School Championships |
| 23. | | 11 | Ben Hosford | 16:59.3PR | MD | Loyola Blakefield | Nov 30
| Nike Southeast Regional (NXN) |
| 24. | | 11 | Connor Coleman | 17:00.0PR | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 25. | | 11 | Kevin Peters | 17:02.3 | MD | Gilman | Nov 6
| MIAA Championships |
| 26. | | 9 | Max Barbour | 17:02.4 | MD | Loyola Blakefield | Nov 30
| Nike Southeast Regional (NXN) |
| 27. | | 11 | Miguel Alonso | 17:04.5PR | MD | Our Lady Of Good Counsel | Nov 30
| Nike Southeast Regional (NXN) |
| 28. | | 10 | Matt Lopez | 17:05.1 | MD | Our Lady Of Good Counsel | Nov 30
| Nike Southeast Regional (NXN) |
| 29. | | 12 | Phil Baldwin | 17:07.0PR | MD | Annapolis Area Christian | Nov 6
| MIAA Championships |
| 30. | | 12 | Kevin Soraci | 17:08.0 | MD | Landon | Oct 26
| IAC, ISL, MAC Championships |
| 31. | 16 | 11 | Chris Jeletic | 17:08.2 | MD | DeMatha Catholic | Sep 21
| Adidas Cross Country Challenge |
| 32. | | 10 | Ned Moreland | 17:11.7 | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 33. | | 11 | Andrew Macdonald | 17:15.3 | MD | Loyola Blakefield | Nov 6
| MIAA Championships |
| 34. | | 11 | Logan Gibbs | 17:17.0PR | MD | Loyola Blakefield | Nov 30
| Nike Southeast Regional (NXN) |
| 35. | | 12 | Patrick Jones | 17:22.0PR | MD | St Maria Goretti | Sep 21
| Mercersburg Invitational |
| 36. | | 9 | Max Barber | 17:23.2PR | MD | Loyola Blakefield | Nov 6
| MIAA Championships |
| 37. | | 10 | Jack McCarthy | 17:24.0 | MD | McDonogh | Oct 12
| Fall Classic at Georgetown Prep |
| 38. | | 12 | Alex Hadley | 17:24.4 | MD | The Heights | Nov 2
| Montgomery County Private School Championship... |
| 39. | | 9 | Jack Chlopak | 17:25.0PR | MD | Landon | Oct 26
| IAC, ISL, MAC Championships |
| 40. | | 12 | Neil Zell | 17:26.2PR | MD | Mount Saint Joseph | Nov 6
| MIAA Championships |
| 41. | | 9 | Lucas Wright | 17:26.3 | MD | McDonogh | Nov 6
| MIAA Championships |
| 42. | | 9 | Jimmy Vazzana | 17:27.0 | MD | Our Lady Of Good Counsel | Sep 28
| Carlisle Invitational |
| 43. | | 10 | Ben Gilbert | 17:28.0 | MD | Landon | Oct 26
| IAC, ISL, MAC Championships |
| 44. | | 11 | Owen Melia | 17:28.7 | MD | Calvert Hall College | Nov 6
| MIAA Championships |
| 45. | | 9 | Timmy Barrick | 17:29.2 | MD | Park | Nov 6
| MIAA Championships |
| 46. | | 12 | Sean Duffy | 17:30.7PR | MD | Loyola Blakefield | Nov 6
| MIAA Championships |
| 47. | | 11 | Jonah Smith | 17:31.0 | MD | The Heights | Oct 12
| Fall Classic at Georgetown Prep |
| 48. | | 11 | Junda Yu | 17:32.0PR | MD | Georgetown Prep | Oct 26
| IAC, ISL, MAC Championships |
| 49. | 16 | 11 | Matt Boulden | 17:33.9 | MD | Archbishop Curley | Aug 31
| Bear Mountain River Run |
| 50. | | 12 | Bendann Murphy | 17:35.3PR | MD | Glenelg Country | Nov 6
| MIAA Championships |
| 51. | | 12 | Evan Wilson | 17:37.4PR | MD | Archbishop Spalding | Nov 6
| MIAA Championships |
| 52. | | 12 | Jack Mutchnik | 17:39.7PR | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 53. | | 10 | Jeremiah Melton | 17:40.1 | MD | Our Lady Of Good Counsel | Oct 19
| Bullis Bulldog Invitational |
| 54. | | 10 | EJ Abass | 17:41.0 | MD | Gilman | Sep 28
| Barnhart Invitational |
| 55. | | 12 | Megan Michael | 17:41.9PR | MD | Mount Saint Joseph | Nov 6
| MIAA Championships |
| 56. | | 12 | Ryan Sevel | 17:47.0 | MD | McDonogh | Nov 6
| MIAA Championships |
| | | 9 | William Powell | 17:47.0 | MD | Landon | Nov 9
| Maryland and DC Private School Championships |
| 58. | | 9 | George Drewyer | 17:48.0 | MD | Our Lady Of Good Counsel | Sep 28
| Carlisle Invitational |
| 59. | | 12 | Matt Harding | 17:48.7PR | MD | Archbishop Spalding | Nov 6
| MIAA Championships |
| 60. | | 10 | Wolfgang Drake | 17:50.0 | MD | Gilman | Sep 28
| Barnhart Invitational |
| 61. | | 12 | Drew Micholas | 17:51.0PR | MD | Bullis | Nov 9
| Maryland and DC Private School Championships |
| 62. | | 12 | Peter Gammell | 17:54.0PR | MD | Mount Airy Christian Acad | Nov 9
| Maryland and DC Private School Championships |
| 63. | | 12 | Chris Filar | 17:54.4PR | MD | Loyola Blakefield | Nov 6
| MIAA Championships |
| 64. | | 12 | Chris Acker | 17:54.9PR | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 65. | 15 | 9 | Reuben Winston | 17:55.0 | MD | Charles E Smith (Lions Upper) | Nov 9
| Maryland and DC Private School Championships |
| 66. | | 11 | Eric Egeli | 17:55.4 | MD | Indian Creek | Nov 6
| MIAA Championships |
| 67. | | 10 | Teddy Strozyk | 17:56.0 | MD | Calvert Hall College | Sep 21
| 62nd Annual Spiked Shoe Invitational |
| | | 12 | Matt Thompson | 17:56.0PR | MD | Loyola Blakefield | Sep 28
| Barnhart Invitational |
| 69. | | 9 | Garrett Voigt | 17:56.3 | MD | Boys Latin | Nov 6
| MIAA Championships |
| 70. | | 10 | Leo Kopp | 17:56.7PR | MD | St Pauls For Boys | Nov 6
| MIAA Championships |
| 71. | 17 | 12 | Dylan Stinner | 17:56.8 | MD | Our Lady Of Good Counsel | Oct 19
| Bullis Bulldog Invitational |
| 72. | | 9 | Nathan Jecelin | 17:58.7 | MD | Archbishop Curley | Oct 5
| Gunpowder Invitational |
| 73. | | 12 | Brooks Andersson | 17:58.9PR | MD | Concordia Prep (Baltimore Lutheran) | Nov 6
| MIAA Championships |
| 74. | | 12 | Theo Leasca | 17:59.0 | MD | Gilman | Sep 7
| Seahawk Invitational |
| 75. | | 11 | Zack Gruzinski | 18:00.6PR | MD | Archbishop Spalding | Nov 6
| MIAA Championships |
| 76. | 17 | 11 | James Jennings | 18:01.7PR | MD | DeMatha Catholic | Oct 5
| Gunpowder Invitational |
| 77. | | 12 | Alex Morton | 18:02.0 | MD | Georgetown Prep | Nov 9
| Maryland and DC Private School Championships |
| 78. | | 12 | Sydney Mukasa | 18:02.2PR | MD | McDonogh | Nov 6
| MIAA Championships |
| 79. | | 11 | Cole Coffay | 18:04.2PR | MD | Boys Latin | Nov 6
| MIAA Championships |
| 80. | | 12 | Josh Bone | 18:04.9PR | MD | Annapolis Area Christian | Nov 6
| MIAA Championships |
| 81. | 17 | 11 | Jarod Barnes | 18:05.0PR | MD | Knowledge and Success Academy | Oct 31
| MPSSAA 1A South Region Championship |
| 82. | | 11 | Will Essl | 18:05.3PR | MD | Mount Saint Joseph | Nov 6
| MIAA Championships |
| 83. | 15 | 10 | Stephen Allen | 18:05.5PR | MD | DeMatha Catholic | Sep 21
| Adidas Cross Country Challenge |
| 84. | | 12 | Robert Wilhelm | 18:06.0PR | MD | Gilman | Nov 9
| Maryland and DC Private School Championships |
| 85. | 16 | 11 | Harry Wandersman | 18:06.3 | MD | Charles E Smith (Lions Upper) | Oct 30
| PVAC Championship |
| 86. | | 11 | Justin Johnson | 18:07.4PR | MD | Bishop McNamara | Sep 28
| P.G.County Cross Country Invitational |
| 87. | | 9 | Cody Kupres | 18:08.1PR | MD | Gilman | Nov 6
| MIAA Championships |
| 88. | | 12 | Nathan Scarff | 18:09.6PR | MD | Concordia Prep (Baltimore Lutheran) | Nov 6
| MIAA Championships |
| 89. | | 10 | Dan Vinton | 18:10.0 | MD | Loyola Blakefield | Sep 28
| Barnhart Invitational |
| | | 10 | Tommy Diehl | 18:10.0PR | MD | Gilman | Nov 9
| Maryland and DC Private School Championships |
| 91. | 16 | 10 | Hunter Fagan | 18:10.6PR | MD | DeMatha Catholic | Sep 21
| Adidas Cross Country Challenge |
| 92. | | 9 | Eric Matzelevich | 18:11.0PR | MD | Bullis | Oct 5
| Octoberfest |
| | | 10 | Dylan Orrell | 18:11.0 | MD | McDonogh | Oct 12
| Fall Classic at Georgetown Prep |
| 94. | | 11 | Jacob Campotelli | 18:11.6 | MD | Mount Saint Joseph | Nov 6
| MIAA Championships |
| 95. | | 12 | Carl Thomas | 18:12.0PR | MD | Saint James | Sep 21
| Mercersburg Invitational |
| | | 10 | Richard Royle | 18:12.0PR | MD | St. Andrew's Episcopal | Oct 26
| IAC, ISL, MAC Championships |
| 97. | | 11 | Brendan Cannon | 18:12.2PR | MD | Archbishop Spalding | Nov 6
| MIAA Championships |
| 98. | | 10 | Ben Kotchick | 18:12.9 | MD | Calvert Hall College | Nov 6
| MIAA Championships |
| 99. | | 10 | Patrick Mullery | 18:13.0 | MD | Georgetown Prep | Oct 26
| IAC, ISL, MAC Championships |
| 100. | | 12 | Caleb Robertson | 18:13.3PR | MD | Annapolis Area Christian | Nov 6
| MIAA Championships |