| | Age | Grade | Athlete | Time | ST | Team | Date | Meet |
| 1. | 17 | 12 | Gavin Sherry | 14:58.6PR | CT | Conard | Sep 25
| Ocean State XC Invitational |
| 2. | 17 | 12 | Callum Sherry | 15:14.7PR | CT | Conard | Sep 25
| Ocean State XC Invitational |
| 3. | 17 | 12 | Luke Anthony | 15:17.3PR | CT | East Lyme | Sep 25
| Ocean State XC Invitational |
| 4. | 17 | 12 | Aidan Puffer | 15:25.0 | CT | Manchester | Nov 5
| CIAC State Open Championships |
| 5. | 18 | 12 | Michael Bohlke | 15:29.0PR | CT | Newington | Nov 5
| CIAC State Open Championships |
| 6. | 18 | 12 | Patrick Gibbons | 15:36.7PR | | Charlotte, NC | Nov 27
| Eastbay South Region Cross Country Championsh... |
| 7. | 17 | 12 | Carver Morgan | 15:39.0PR | CT | Avon | Sep 21
| Conard, Glastonbury @ Avon |
| 8. | 17 | 12 | Sean Kennedy-Wonneb... | 15:42.4PR | CT | Hale Ray | Oct 1
| 62nd Nonnewaug XC Invitational |
| 9. | 17 | 12 | Justin Cascio | 15:51.5PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 10. | 18 | 12 | Eamon Burke | 15:55.0PR | CT | Xavier (CT) | Nov 5
| CIAC State Open Championships |
| 11. | | 12 | Nathan Cramer | 15:55.1PR | CT | Fairfield Ludlowe | Sep 25
| 9th Winding Trails XC Invitational |
| 12. | 18 | 12 | Jack O'Keefe | 15:56.2PR | CT | Daniel Hand | Sep 18
| 10th Connecticut River Valley Invitational |
| 13. | | 12 | Joseph Accurso | 15:58.0PR | CT | Glastonbury | Sep 21
| Conard, Glastonbury @ Avon |
| 14. | 16 | 11 | Francis Porrini III | 15:59.0PR | CT | Bristol Central | Oct 5
| Maloney vs Bristol Central & Lewis Mills |
| 15. | 18 | 12 | Jack Martin | 16:02.0 | CT | Avon | Nov 5
| CIAC State Open Championships |
| 16. | | 12 | Lucas Pombo | 16:04.3PR | CT | Brunswick | Nov 1
| Fairchester Athletic Association Championship... |
| 17. | 17 | 12 | Nikita Omelchenko | 16:05.0PR | CT | Wilbur Cross | Nov 5
| CIAC State Open Championships |
| 18. | 17 | 12 | Walker Beverly | 16:07.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 19. | 15 | 10 | Steven Hergenrother | 16:13.0 | CT | Ridgefield | Nov 5
| CIAC State Open Championships |
| 20. | 17 | 12 | Matthew McDonough | 16:15.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| | | 12 | Zachary Taubman | 16:15.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| 22. | | 12 | Mason Beaudette | 16:16.0PR | CT | Amity | Nov 5
| CIAC State Open Championships |
| | 16 | 10 | Luke Davis | 16:16.0 | CT | Simsbury | Nov 5
| CIAC State Open Championships |
| 24. | 17 | 12 | Sean Barkasy | 16:17.4PR | CT | Manchester | Oct 19
| CCC Cross Country Championships |
| 25. | 17 | 12 | Davis Anderson | 16:19.0PR | CT | Simsbury | Sep 21
| Hall vs Farmington, Simsbury |
| 26. | | 12 | Mohammed Abunar | 16:20.0PR | CT | Trumbull | Oct 20
| FCIAC XC Championships |
| 27. | 17 | 12 | Luke Stoeffler | 16:22.0PR | CT | Tolland | Oct 9
| 37th Wickham Park XC Invitational |
| | | 12 | Jack Dovaras | 16:22.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| | | 12 | Evan Boland | 16:22.0PR | CT | E.O. Smith | Nov 5
| CIAC State Open Championships |
| 30. | 16 | 10 | Griffin Mandirola | 16:23.0 | CT | Suffield | Nov 5
| CIAC State Open Championships |
| 31. | 15 | 10 | Devon Rosemark | 16:23.4PR | CT | Danbury Hatters HCYS Track & XC Club | Nov 14
| USATF Connecticut Association Junior Olympic ... |
| 32. | 17 | 12 | William Calhoun | 16:25.9PR | CT | RHAM | Sep 18
| 10th Connecticut River Valley Invitational |
| 33. | -1 | 11 | Michael Byrnes | 16:27.0 | CT | Wilton | Oct 20
| FCIAC XC Championships |
| 34. | | 12 | Daniel Hilmer | 16:27.2PR | CT | Daniel Hand | Sep 18
| 10th Connecticut River Valley Invitational |
| 35. | | 11 | Ryan Gagne | 16:30.0 | CT | Wethersfield | Nov 5
| CIAC State Open Championships |
| | 15 | 10 | Isaac Mahler | 16:30.0 | CT | Hall | Nov 5
| CIAC State Open Championships |
| 37. | 17 | 12 | Jalen St.Fort | 16:31.0PR | CT | Staples | Oct 20
| FCIAC XC Championships |
| 38. | 17 | 12 | Grayson Borla | 16:32.0PR | CT | Southington | Oct 12
| Southington at NW Catholic |
| | | 12 | Benjamin Mickool | 16:32.0 | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 40. | | 11 | AJ Taborsak | 16:32.3 | CT | New Milford | Sep 18
| Dan Purdy Invitational |
| 41. | | 11 | Harrison Grenier | 16:32.8 | CT | Daniel Hand | Sep 18
| 10th Connecticut River Valley Invitational |
| 42. | 16 | 10 | Collin Walsh | 16:35.0 | CT | New Milford | Nov 5
| CIAC State Open Championships |
| 43. | 17 | 11 | Avery Allen | 16:36.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| | 17 | 12 | Brody Santagata | 16:36.0 | CT | Xavier (CT) | Nov 5
| CIAC State Open Championships |
| 45. | | 12 | Joseph Callanan | 16:38.0PR | CT | Fairfield Warde | Oct 20
| FCIAC XC Championships |
| | | 12 | Caleb Freeman | 16:38.0PR | CT | Haddam-Killingworth | Nov 5
| CIAC State Open Championships |
| | | 12 | Parker Paragas | 16:38.0PR | CT | Amity | Nov 5
| CIAC State Open Championships |
| 48. | 16 | 11 | Michael Kraszewski | 16:39.0 | CT | Hale Ray | Oct 1
| 62nd Nonnewaug XC Invitational |
| | 18 | 12 | Zachary Jelinek | 16:39.0PR | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| | 16 | 11 | Nathaniel Aronson | 16:39.0 | CT | Hall | Nov 19
| Run Rabbit Run 2021 |
| 51. | 17 | 12 | Calvin Young | 16:41.0PR | CT | Joel Barlow | Nov 5
| CIAC State Open Championships |
| 52. | | 12 | Evan O'Rourke | 16:42.0PR | CT | Darien | Oct 20
| FCIAC XC Championships |
| 53. | | 12 | Erik Kuselias | 16:44.0PR | CT | Notre Dame-West Haven | Sep 14
| Notre Dame/SHA Duals |
| 54. | | 11 | Liam Fedigan | 16:45.0 | CT | Jonathan Law | Sep 14
| Notre Dame/SHA Duals |
| 55. | | 12 | Bronson Vo | 16:46.0PR | CT | Trumbull | Oct 20
| FCIAC XC Championships |
| 56. | 18 | 12 | William Bennett | 16:46.7PR | CT | King | Oct 20
| Fairchester AA Meet #3 |
| 57. | | 12 | Angel Perez | 16:48.0PR | CT | Fairfield Prep | Sep 14
| Lauralton Hall/F.Prep, Amity, Branford @Foran |
| | 17 | 11 | Jake Nafis | 16:48.0 | CT | Southington | Oct 12
| Southington at NW Catholic |
| | | 12 | Henri Vieltojarvi | 16:48.0PR | CT | Ridgefield | Oct 20
| FCIAC XC Championships |
| 60. | 16 | 10 | Benjamin Lorenz | 16:50.0 | CT | Staples | Oct 20
| FCIAC XC Championships |
| | | 11 | Brayden Bayek | 16:50.0 | CT | Rocky Hill | Nov 5
| CIAC State Open Championships |
| 62. | 17 | 12 | Joshua Lesniak | 16:51.0PR | CT | Xavier (CT) | Nov 5
| CIAC State Open Championships |
| 63. | 16 | 11 | Ethan Manfredi | 16:52.6PR | CT | Norwich Free Academy | Sep 25
| Ocean State XC Invitational |
| 64. | | 12 | Ethan Carty | 16:53.0 | CT | Fairfield Ludlowe | Oct 20
| FCIAC XC Championships |
| | 15 | 10 | Christian Zawislack | 16:53.0 | CT | Greenwich | Oct 20
| FCIAC XC Championships |
| | 16 | 11 | Nicholas Montana | 16:53.0 | CT | Daniel Hand | Nov 5
| CIAC State Open Championships |
| 67. | | 11 | Alexander Ushchak | 16:54.0 | CT | Xavier (CT) | Nov 5
| CIAC State Open Championships |
| 68. | | 12 | Anthony Galicia | 16:54.6PR | CT | Sheehan | Sep 18
| 10th Connecticut River Valley Invitational |
| 69. | 16 | 11 | Colin Goldschmidt | 16:56.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | 18 | 12 | Lucas Hester | 16:56.0PR | CT | Avon | Oct 5
| Hall vs Avon, NW Catholic |
| 71. | | 12 | Joshua Burr | 16:58.0 | CT | Hall | Sep 21
| Hall vs Farmington, Simsbury |
| | | 12 | Jack O'Donnell | 16:58.0PR | CT | Avon | Sep 21
| Conard, Glastonbury @ Avon |
| | | 12 | Liam Scully | 16:58.0PR | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 74. | | 10 | Tyler Caron | 16:59.0PR | CT | Cheshire | Nov 5
| CIAC State Open Championships |
| 75. | 16 | 11 | Nick Yoo | 16:59.3 | CT | Darien | Oct 12
| Trumbull/Stamford/Darien at Ludlowe |
| 76. | 16 | 11 | Alex Cole | 16:59.7PR | CT | Watertown | Oct 1
| 62nd Nonnewaug XC Invitational |
| 77. | 17 | 12 | Colin Slavin | 17:00.0PR | CT | Woodland | Oct 20
| NVL XC Championships |
| 78. | | 11 | Al Nickerson | 17:00.1 | CT | Greenwich Country Day | Oct 20
| Fairchester AA Meet #3 |
| 79. | | 11 | Noah Burgio | 17:02.0PR | CT | Conard | Sep 21
| Conard, Glastonbury @ Avon |
| 80. | 16 | 11 | Michael Strain | 17:02.2 | CT | Griswold | Sep 25
| 9th Winding Trails XC Invitational |
| 81. | 16 | 11 | Ethan Striff-Cave | 17:03.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| | 15 | 10 | Parker Broderick | 17:03.0 | CT | Fairfield Warde | Oct 9
| 37th Wickham Park XC Invitational |
| 83. | | 11 | Seamus Reidy | 17:03.7 | CT | Immaculate | Oct 2
| Brewster Bear Cross Country Classic |
| 84. | | 12 | William Rodrigues | 17:04.0PR | CT | Shelton | Nov 5
| CIAC State Open Championships |
| 85. | | 12 | Samuel Simko | 17:05.0 | CT | Xavier (CT) | Nov 5
| CIAC State Open Championships |
| 86. | | 11 | Michael Masotti | 17:06.0 | CT | Guilford | Nov 5
| CIAC State Open Championships |
| 87. | | 11 | Damian Smith | 17:07.0PR | CT | Ellington | Nov 5
| CIAC State Open Championships |
| 88. | 15 | 10 | David Carillo | 17:07.1 | CT | Trumbull | Sep 29
| Trumbull/Ridgefield/Danbury at New Canaan |
| 89. | 16 | 10 | Jameson Sederquist | 17:07.3PR | CT | Lewis Mills | Oct 1
| 62nd Nonnewaug XC Invitational |
| 90. | | 11 | Joseph Dane | 17:07.9PR | CT | Holy Cross | Oct 1
| 62nd Nonnewaug XC Invitational |
| 91. | | 10 | Parker Cook | 17:08.0 | CT | Old Saybrook | Sep 18
| 10th Connecticut River Valley Invitational |
| | | 12 | Nicholas Bailey | 17:08.0PR | CT | Avon | Oct 12
| Farmington @ Avon |
| 93. | | 12 | Alex Harrington | 17:08.4 | CT | Staples | Sep 29
| Greenwich/McMahon/Ludlowe at Staples |
| 94. | | 11 | Apurv Manjreker | 17:09.0 | CT | Hall | Oct 5
| Hall vs Avon, NW Catholic |
| 95. | | 12 | Robert Constable | 17:09.4PR | CT | Daniel Hand | Sep 18
| 10th Connecticut River Valley Invitational |
| 96. | 15 | 10 | Jacob Kozar | 17:09.7PR | CT | New Canaan Blazers | Nov 14
| USATF Connecticut Association Junior Olympic ... |
| 97. | 15 | 10 | Jack Mattingly | 17:09.9 | CT | E.O. Smith | Sep 18
| 10th Connecticut River Valley Invitational |
| | 13 | 8 | Nathan Lee | 17:09.9 | CT | Brunswick | Oct 6
| Fairchester AA Meet #2 |
| 99. | | 11 | Brendan Fant | 17:10.0 | CT | East Lyme | Nov 5
| CIAC State Open Championships |
| | | 12 | Owen Delisle | 17:10.0PR | CT | Portland | Nov 5
| CIAC State Open Championships |
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