| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 17 | 12 | Steven Hergenrother | 14:52.6PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 2. | 15 | 10 | Alex Fisher | 15:08.6PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 3. | 17 | 12 | Isaac Mahler | 15:29.7PR | CT | Hall | Sep 23
| 16th Ocean State XC Invitational |
| 4. | 16 | 11 | Soheib Dissa | 15:31.3PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 5. | 17 | 11 | Jack Ouellette | 15:32.3PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 6. | 17 | 12 | Jack Mattingly | 15:32.4PR | CT | E.O. Smith | Sep 30
| Maine XC Festival of Champions |
| 7. | 18 | 12 | Griffin Mandirola | 15:33.7PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 8. | | 11 | Charles Lovett | 15:37.8PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 9. | 17 | 12 | Parker Broderick | 15:40.0PR | CT | Fairfield Warde | Oct 18
| FCIAC Cross Country Championships |
| 10. | 16 | 11 | Owen Martin | 15:42.9PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 11. | | 11 | Sullivan Dunn | 15:43.1PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 12. | | 12 | Parker Cook | 15:45.2PR | CT | Old Saybrook | Oct 19
| Shoreline Cross Country Championships |
| 13. | | 11 | Matthew Kraszewski | 15:45.5PR | CT | Hale Ray | Oct 19
| Shoreline Cross Country Championships |
| 14. | | 11 | Magnus Manley | 15:48.6PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 15. | 16 | 11 | Samuel Zwick-Lavins... | 15:50.0PR | CT | Staples | Oct 18
| FCIAC Cross Country Championships |
| | 15 | 10 | Nathan Lee | 15:50.0PR | CT | Brunswick | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 17. | 17 | 11 | Morgan Samuel | 15:51.0PR | CT | Staples | Oct 18
| FCIAC Cross Country Championships |
| 18. | 16 | 11 | Sean McCauley | 15:55.6PR | CT | East Lyme | Nov 11
| New England Interscholastic XC Championships |
| 19. | | 11 | Evan Bureau | 15:56.9PR | CT | Bethel | Nov 11
| New England Interscholastic XC Championships |
| 20. | 18 | 12 | John Glidden | 15:58.0PR | CT | Rockville | Sep 23
| 16th Ocean State XC Invitational |
| | 17 | 12 | Elias Alvarado | 15:58.0PR | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| 22. | 17 | 11 | Christian Menounos | 15:58.2PR | CT | Woodstock Academy | Oct 7
| MSTCA Bay State Invitational |
| 23. | | 12 | Colby Bornstein | 15:58.7PR | CT | Tolland | Nov 11
| New England Interscholastic XC Championships |
| 24. | | 11 | Michael Komisky | 15:59.0PR | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| | 18 | 12 | Collin Walsh | 15:59.0 | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 26. | 16 | 11 | Jack Cozean | 15:59.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 27. | 17 | 11 | Kyle Jeffers | 16:02.0PR | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| 28. | 17 | 12 | Christopher Bishop | 16:03.0PR | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| | 16 | 10 | Luke Cushing | 16:03.0PR | CT | Amity | Nov 6
| CIAC State Open Boys Championship |
| 30. | 17 | 12 | Devon Rosemark | 16:03.2 | CT | Danbury | Nov 11
| New England Interscholastic XC Championships |
| 31. | 14 | 9 | Tycen LaBelle | 16:03.3PR | CT | Griswold | Nov 11
| New England Interscholastic XC Championships |
| 32. | 17 | 12 | Nico Boyle | 16:06.7PR | CT | North Haven | Nov 11
| New England Interscholastic XC Championships |
| 33. | | 12 | Cameron Nephew | 16:07.1PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 34. | 17 | 11 | Trevor Fuller | 16:07.6PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 35. | 17 | 11 | Ryan Boulanger | 16:08.8PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 36. | 17 | 12 | David Carillo | 16:11.0 | CT | Trumbull | Oct 18
| FCIAC Cross Country Championships |
| | 16 | 10 | Copey (Copeland) Ro... | 16:11.0PR | CT | Hotchkiss | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 38. | 17 | 12 | Harjaap Singh | 16:12.0PR | CT | Trumbull | Oct 18
| FCIAC Cross Country Championships |
| 39. | 18 | 12 | Luke Davis | 16:12.8 | CT | Simsbury | Sep 19
| Conard, Simsbury @ Avon |
| 40. | | 11 | Brendan Cook | 16:14.1PR | CT | E.O. Smith | Sep 30
| Maine XC Festival of Champions |
| 41. | 16 | 11 | Matthew Lara | 16:15.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 42. | | 12 | John Larkin | 16:16.7PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| | 17 | 12 | Daniel Coyne | 16:16.7PR | CT | Simsbury | Nov 11
| New England Interscholastic XC Championships |
| 44. | 15 | 10 | Daniel McCourt | 16:17.3PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| | 17 | 11 | Shepard Livingston | 16:17.3PR | | 05-Unattached | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 46. | 17 | 12 | Christian Zawislack | 16:18.5 | CT | Greenwich | Oct 8
| Brewster Bear XC Classic (POSTPONED TO SUNDAY... |
| 47. | 17 | 12 | Benjamin Daniels | 16:20.0 | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 48. | 18 | 12 | Donovan Crowley | 16:22.0PR | CT | Avon Old Farms | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 49. | 17 | 11 | Dylan Bathrick | 16:22.4PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 50. | 18 | 12 | Benjamin Lorenz | 16:23.0 | CT | Staples | Oct 28
| CIAC Division LL Boys Championship |
| | | 11 | Jack Muhlhauser | 16:23.0PR | CT | Loomis Chaffee | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 52. | | 12 | Nathan Bergman | 16:24.0PR | CT | East Lyme | Sep 19
| ECC Tri Meet EL/Montville/Woodstock |
| 53. | | 9 | Edward (Teddy) Hojl... | 16:26.0PR | CT | Brunswick | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 54. | 16 | 11 | Jilali Benjdid | 16:26.8PR | CT | East Lyme | Sep 23
| 16th Ocean State XC Invitational |
| 55. | | 11 | Matthew Carrier | 16:28.0PR | CT | East Lyme | Sep 19
| ECC Tri Meet EL/Montville/Woodstock |
| | | 12 | Colin Carpenter | 16:28.0PR | CT | Wooster (Danbury) | Nov 3
| HVAL Championship |
| 57. | | 10 | Lorenzo Lopes | 16:28.6PR | CT | Immaculate | Oct 18
| SWC Championship |
| 58. | | 11 | William Liebler | 16:29.2PR | CT | Southington | Sep 23
| 16th Ocean State XC Invitational |
| 59. | 15 | 10 | Crawford Cauthen | 16:29.8PR | CT | Glastonbury | Sep 30
| Maine XC Festival of Champions |
| 60. | 18 | 12 | Ben Schipul | 16:30.0PR | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 61. | 16 | 11 | Alexander Glenn | 16:30.2PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| | | 11 | Evan LoPresti | 16:30.2PR | CT | East Hampton | Oct 19
| Shoreline Cross Country Championships |
| 63. | 16 | 11 | Spencer Slayton | 16:30.7PR | CT | E.O. Smith | Sep 30
| Maine XC Festival of Champions |
| 64. | | 12 | Luke Hedges | 16:31.2PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 65. | | 11 | Evan Belles | 16:31.8PR | CT | Brookfield | Sep 23
| 16th Ocean State XC Invitational |
| 66. | | 12 | Cameron Miles | 16:32.0PR | CT | Weston | Nov 6
| CIAC State Open Boys Championship |
| 67. | 18 | 12 | Evan Piccioli | 16:34.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 68. | 2 | 12 | Alex Cohen | 16:35.0 | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 69. | | 11 | Ben Farmer | 16:36.0PR | CT | Notre Dame-West Haven | Sep 19
| ND/SHA Duals |
| 70. | 16 | 10 | Pearse McInerney | 16:36.2PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 71. | | 11 | Ian Schmeelk | 16:37.0PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| | 17 | 11 | Tate Celebi | 16:37.0PR | CT | Taft | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| | | 12 | Ciaran Groom | 16:37.0PR | CT | Hotchkiss | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 74. | 17 | 11 | William Lancaster | 16:38.2 | CT | Avon | Sep 19
| Conard, Simsbury @ Avon |
| 75. | | 11 | Everett Miller | 16:38.3PR | CT | Old Saybrook | Oct 19
| Shoreline Cross Country Championships |
| 76. | | 12 | Gabriel Montoya | 16:38.5PR | CT | E.O. Smith | Sep 30
| Maine XC Festival of Champions |
| 77. | 26 | 10 | Sam Leone | 16:39.6PR | CT | East Lyme | Sep 23
| 16th Ocean State XC Invitational |
| 78. | 16 | 11 | Connor Garrett | 16:40.5PR | CT | Hamden | Oct 18
| SCC Cross Country Championships |
| 79. | | 11 | Gabriel Nodland | 16:40.6PR | CT | Hale Ray | Oct 19
| Shoreline Cross Country Championships |
| 80. | 16 | 11 | Grant Bigger | 16:41.0PR | CT | Conard | Oct 11
| Conard vs Hall |
| 81. | 15 | 10 | Nathan Yingling | 16:42.0PR | CT | Hall | Oct 11
| Conard vs Hall |
| | 16 | 11 | Calum Madigan | 16:42.0PR | CT | Staples | Oct 18
| FCIAC Cross Country Championships |
| 83. | 17 | 11 | Sebastian Halpern | 16:43.1PR | CT | Wilbur Cross | Oct 18
| SCC Cross Country Championships |
| 84. | | 11 | Aaron Allen | 16:43.2PR | CT | Hale Ray | Oct 19
| Shoreline Cross Country Championships |
| 85. | | 10 | Aidan Nelson | 16:43.5PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 86. | | 12 | Nwang Choegyal | 16:44.8PR | CT | Old Saybrook | Oct 19
| Shoreline Cross Country Championships |
| 87. | | 10 | Hayden Burke | 16:45.0PR | CT | Portland | Oct 19
| Shoreline Cross Country Championships |
| 88. | | 12 | William Connolly | 16:46.2PR | CT | E.O. Smith | Sep 30
| Maine XC Festival of Champions |
| 89. | | 11 | Tyler Deme | 16:46.4PR | CT | Sheehan | Oct 18
| SCC Cross Country Championships |
| 90. | | 12 | Jackson Sobelman | 16:46.5PR | CT | Joel Barlow | Oct 18
| SWC Championship |
| 91. | 18 | 12 | Zachary Barth | 16:46.8PR | CT | Lewis Mills | Sep 30
| 64th Nonnewaug XC Invitational |
| | | 12 | Coleman Love | 16:46.8PR | CT | Guilford | Oct 10
| Hamden VS Career, Guilford, & Sheehan |
| 93. | 16 | 11 | Donovan Connole | 16:47.0 | CT | Hall | Oct 11
| Conard vs Hall |
| 94. | | 11 | Kyle McCarron | 16:47.3PR | CT | Housatonic Valley Regional | Sep 20
| 35th Going to the Sun XC Invitational |
| 95. | | 10 | Breckin Burke | 16:48.2PR | CT | Portland | Oct 19
| Shoreline Cross Country Championships |
| 96. | | 11 | Raza Malik | 16:49.1PR | CT | Glastonbury | Sep 30
| Maine XC Festival of Champions |
| 97. | | 12 | Charles Williamson | 16:50.0PR | CT | Fairfield Warde | Oct 18
| FCIAC Cross Country Championships |
| | 15 | 10 | Matteo Chiesara | 16:50.0 | CT | Greenwich | Nov 25
| NXR Northeast & New York Regional Championshi... |
| 99. | | 9 | Cooper Grace | 16:51.0PR | CT | Hotchkiss | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 100. | 0 | 11 | Colton Sallum | 16:51.7PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
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