| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 18 | 12 | Griffin Mandirola | 15:33.7PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 2. | 16 | 11 | Jack Cozean | 15:59.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 3. | 14 | 9 | Tycen LaBelle | 16:03.3PR | CT | Griswold | Nov 11
| New England Interscholastic XC Championships |
| 4. | 16 | 11 | Matthew Lara | 16:15.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 5. | 15 | 10 | Daniel McCourt | 16:17.3PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 6. | 17 | 11 | Dylan Bathrick | 16:22.4PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 7. | | 12 | Luke Hedges | 16:31.2PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 8. | 15 | 10 | Cash Smigel | 16:53.7PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 9. | 15 | 10 | Brian Smith | 17:02.3PR | CT | Rocky Hill | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 10. | 15 | 10 | Alex Frederickson | 17:04.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 11. | | 12 | Samuel Ambrocio | 17:09.0PR | CT | Woodland | Nov 6
| CIAC State Open Boys Championship |
| 12. | | 11 | Daniel DiTunno | 17:12.2PR | CT | Rocky Hill | Sep 15
| Blue Dragon Invitational |
| 13. | 15 | 10 | Jake Cenatiempo | 17:15.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |
| 14. | 16 | 11 | Sawyer DiMatteo | 17:18.7PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 15. | 16 | 11 | Jake Ferrare | 17:27.0PR | CT | Holy Cross | Oct 28
| CIAC Division SS Boys Championship |
| 16. | 16 | 11 | Corey Christensen | 17:28.0PR | CT | Rocky Hill | Nov 6
| CIAC State Open Boys Championship |
| 17. | 15 | 9 | Nathan Peskin | 17:33.0PR | CT | Suffield | Oct 28
| CIAC Division SS Boys Championship |
| 18. | | 11 | Colin Monahan | 17:36.2PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 19. | | 11 | Ayden Collura | 17:39.0PR | CT | Rocky Hill | Sep 15
| Blue Dragon Invitational |
| 20. | 17 | 11 | Andrew Organ | 17:46.0PR | CT | Suffield | Oct 28
| CIAC Division SS Boys Championship |
| 21. | | 12 | Zackary Scott | 17:46.3PR | CT | Valley Regional | Oct 19
| Shoreline Cross Country Championships |
| 22. | | 12 | Jaden Smith | 17:54.0PR | CT | Bloomfield | Oct 10
| Bloomfield @ Windsor |
| 23. | | 10 | Patrick Monahan | 17:54.9PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 24. | 18 | 12 | William Thomsen | 17:55.2PR | CT | Northwestern | Oct 19
| Berkshire League XC Championships |
| 25. | | 11 | Bryce Figueiredo | 17:56.6PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 26. | | 12 | Coleman Promotico | 17:58.6PR | CT | Holy Cross | Sep 30
| 64th Nonnewaug XC Invitational |
| 27. | 15 | 9 | Dylan Bailey | 17:59.9PR | | 05-Unattached | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 28. | | 10 | Trevor Genthe | 18:01.0PR | CT | Woodland | Oct 28
| CIAC Division SS Boys Championship |
| 29. | 14 | 9 | Evan Berardino | 18:01.9PR | CT | Haddam-Killingworth | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 30. | | 12 | Tanmay Thaker | 18:02.0PR | CT | University | Oct 13
| 11th Harry Geraghty XC Invite |
| | 16 | 11 | Gabriel Diamante | 18:02.0PR | CT | Woodland | Oct 28
| CIAC Division SS Boys Championship |
| 32. | | 11 | Logan Simons | 18:02.9PR | CT | Rocky Hill | Oct 17
| CCC XC Championships |
| 33. | | 12 | Jack Brehler | 18:04.0PR | CT | Montville | Sep 15
| Wheeler Invitational |
| 34. | | 11 | Keller Tobey | 18:04.8 | CT | Suffield | Oct 18
| NCCC Championship Meet |
| 35. | | 9 | Aiden Hopkins | 18:08.5PR | CT | Suffield | Oct 18
| NCCC Championship Meet |
| 36. | 14 | 9 | Boden Paul | 18:17.9PR | CT | Bacon Academy | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 37. | 15 | 10 | Michael Dickey | 18:19.4PR | CT | Bacon Academy | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 38. | | 11 | Noah Spagnola | 18:22.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |
| 39. | 16 | 11 | Brady Decastro | 18:23.5PR | CT | Stonington | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 40. | | 12 | Walter Withrow | 18:24.0PR | CT | St. Joseph | Oct 18
| FCIAC Cross Country Championships |
| 41. | | 11 | Ryan DePaulo | 18:25.9PR | CT | Holy Cross | Sep 30
| 64th Nonnewaug XC Invitational |
| 42. | | 11 | Ben Farroni | 18:27.6PR | CT | Suffield | Oct 18
| NCCC Championship Meet |
| 43. | | 12 | Joseph Colangelo | 18:28.4 | CT | Suffield | Oct 18
| NCCC Championship Meet |
| 44. | | 10 | Jason Lin | 18:31.3PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 45. | | 12 | Cooper Piesco | 18:31.7 | CT | New Fairfield | Oct 18
| SWC Championship |
| 46. | | 11 | Otto Gotberg | 18:32.1PR | CT | Granby Memorial | Oct 18
| NCCC Championship Meet |
| 47. | | 9 | Paul Birkmeyer | 18:32.3PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 48. | 14 | 9 | Gavin Baron | 18:33.6PR | CT | Granby Memorial | Oct 18
| NCCC Championship Meet |
| 49. | | 12 | Maxwell Brown | 18:35.8PR | CT | Griswold | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 50. | | 12 | Matthew Krekoska | 18:36.0PR | CT | St. Joseph | Oct 18
| FCIAC Cross Country Championships |
| | | 11 | Alexander Gau | 18:36.0PR | CT | Rocky Hill | Nov 6
| CIAC State Open Boys Championship |
| 52. | 17 | 12 | Carrington Flynn | 18:37.8 | CT | New Fairfield | Oct 18
| SWC Championship |
| 53. | 14 | 9 | Sean Silva | 18:40.8PR | CT | Griswold | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 54. | | 11 | Patrick Cugliari | 18:41.8PR | CT | Holy Cross | Sep 20
| 35th Going to the Sun XC Invitational |
| 55. | | 9 | Wyatt Voegtli | 18:42.0PR | CT | Haddam-Killingworth | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 56. | 17 | 12 | Evan Bomengen | 18:44.7PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 57. | | 11 | Owen Pothier | 18:45.0PR | CT | Plainfield | Sep 15
| Wheeler Invitational |
| 58. | | 12 | Brody Landheer | 18:45.7 | CT | Granby Memorial | Oct 18
| NCCC Championship Meet |
| 59. | 17 | 12 | Ryan Solerti | 18:51.1PR | CT | Seymour | Sep 30
| 64th Nonnewaug XC Invitational |
| 60. | 15 | 10 | Corbin Fretz | 18:55.5PR | CT | Nonnewaug | Sep 30
| 64th Nonnewaug XC Invitational |
| 61. | | 10 | Jake Wolfradt | 18:56.6PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 62. | | 11 | Kyle Lanese | 18:57.5 | CT | Holy Cross | Sep 30
| 64th Nonnewaug XC Invitational |
| 63. | 15 | 10 | Owen Lombardi | 18:57.8PR | CT | Morgan | Oct 19
| Shoreline Cross Country Championships |
| 64. | | 11 | Aidan Devaney | 18:58.0PR | CT | Holy Cross | Sep 20
| 35th Going to the Sun XC Invitational |
| 65. | 17 | 12 | Ryan Wolanski | 19:02.8PR | CT | Western Connecticut Flash | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 66. | | 10 | Anthony Frederickso... | 19:03.5PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 67. | | 12 | Benjamin Weber | 19:05.9 | CT | Granby Memorial | Oct 18
| NCCC Championship Meet |
| 68. | | 11 | Anaia Abraham | 19:06.2PR | CT | Rocky Hill | Sep 15
| Blue Dragon Invitational |
| 69. | | 12 | Ethan Perez | 19:08.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |
| 70. | | 10 | Ray O'Connell | 19:08.5PR | CT | Holy Cross | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 71. | 18 | 12 | Garrett Dolin | 19:12.5PR | CT | Canton | Oct 18
| NCCC Championship Meet |
| 72. | | 10 | Ian McClain | 19:12.7PR | CT | Bacon Academy | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 73. | | 10 | Isaiah Mason | 19:14.5PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 74. | | 12 | Alexander Gibbons | 19:15.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |
| 75. | 17 | 12 | Aaron Fidrych | 19:15.6PR | CT | Bacon Academy | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 76. | 17 | 12 | Reid Sunshine | 19:16.0 | CT | Suffield | Sep 9
| 42nd Stratton Brook XC Invitational |
| 77. | | 11 | Ethan Lindquist | 19:17.0 | CT | Canton | Oct 28
| CIAC Division SS Boys Championship |
| 78. | 15 | 10 | Adam Livingston | 19:17.2PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 79. | | 9 | Tyler Traczyk | 19:17.8PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 80. | 17 | 12 | Ja'Mari Manson | 19:18.0 | CT | Bloomfield | Oct 10
| Bloomfield @ Windsor |
| 81. | | 12 | Jay Wikarska | 19:18.6PR | CT | Bacon Academy | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 82. | | 11 | Nathan Dhillon | 19:20.0PR | CT | Montville | Sep 15
| Wheeler Invitational |
| 83. | | 11 | Alexander Joseph | 19:22.0PR | CT | Montville | Sep 15
| Wheeler Invitational |
| 84. | 15 | 10 | Joshua Montgomery | 19:25.1PR | CT | Griswold | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 85. | | 9 | Ryan Organ | 19:27.8PR | CT | Suffield | Oct 18
| NCCC Championship Meet |
| 86. | | 11 | Julian Benham | 19:29.0PR | CT | Northwestern | Sep 26
| Nonnewaug vs Northwestern and Shepaug |
| | 16 | 11 | Cole Fontaine | 19:29.0PR | CT | Griswold | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| | 15 | 10 | Thatcher Budris | 19:29.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |
| 89. | | 10 | Oliver Proctor | 19:30.9PR | CT | Valley Regional | Oct 24
| Old Saybrook Frosh-Soph Invitational |
| 90. | | 10 | George Redford III | 19:34.4PR | CT | Canton | Oct 18
| NCCC Championship Meet |
| 91. | | 9 | August Gotberg | 19:35.5PR | CT | Granby Memorial | Oct 18
| NCCC Championship Meet |
| 92. | | 12 | Anthony Pierce | 19:38.0PR | CT | Suffield | Oct 11
| Ellington at Suffield |
| 93. | | 10 | Jethro Ehrlich | 19:44.3PR | CT | University | Oct 13
| 11th Harry Geraghty XC Invite |
| 94. | | 11 | Bryan Gallino | 19:46.1PR | CT | Holy Cross | Sep 30
| 64th Nonnewaug XC Invitational |
| | | 11 | Soren Tassmer | 19:46.1PR | CT | Haddam-Killingworth | Oct 19
| Shoreline Cross Country Championships |
| 96. | 15 | 10 | Jessie Singleton Jr... | 19:51.0PR | CT | Bloomfield | Oct 10
| Bloomfield @ Windsor |
| 97. | | 11 | Christian Lozito | 19:51.2 | CT | Holy Cross | Sep 30
| 64th Nonnewaug XC Invitational |
| 98. | 17 | 11 | Lucas Witkowski | 19:53.8PR | CT | Cromwell | Oct 19
| Shoreline Cross Country Championships |
| 99. | 14 | 9 | Xzavier De La Rosa | 19:54.8PR | CT | Griswold | Oct 10
| Griswold, Bacon Academy, Killingly @ Griswold |
| 100. | | 12 | Dylan Duda | 19:55.0PR | CT | Nonnewaug | Oct 10
| Nonnewaug vs Litchfield & Wamogo |