| | 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. | 17 | 12 | Byron Grevious | 14:56.0PR | NH | Phillips Exeter Academy | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 3. | 15 | 10 | Alex Fisher | 15:08.6PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 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. | 18 | 12 | Griffin Mandirola | 15:33.7PR | | Unattached | Nov 25
| Foot Locker Cross Country Northeast Regional ... |
| 7. | 16 | 11 | Owen Martin | 15:42.9PR | CT | Xavier (CT) | Oct 7
| Great American XC Festival, Presented by Garm... |
| 8. | 15 | 10 | Nathan Lee | 15:50.0PR | CT | Brunswick | Nov 11
| NEPSTA Division 1 Cross-Country Championships |
| 9. | 18 | 12 | Collin Walsh | 15:59.0 | CT | New Milford | Nov 6
| CIAC State Open Boys Championship |
| 10. | 17 | 12 | Devon Rosemark | 16:03.2 | CT | Danbury | Nov 11
| New England Interscholastic XC Championships |
| 11. | 17 | 11 | Ryan Boulanger | 16:08.8PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 12. | 15 | 10 | Lorenzo Lopes | 16:16.6PR | CT | Danbury Hatters HCYS Track & XC Club | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 13. | 16 | - | Braden Barber | 16:18.6PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 14. | 16 | 11 | Alexander Glenn | 16:30.2PR | CT | Ridgefield | Oct 7
| Great American XC Festival, Presented by Garm... |
| 15. | 15 | 10 | Matteo Chiesara | 16:50.0 | CT | Greenwich | Nov 25
| NXR Northeast & New York Regional Championshi... |
| 16. | 14 | 9 | Beau Kociszewski | 16:53.5PR | CT | Thomaston | Sep 30
| 64th Nonnewaug XC Invitational |
| 17. | 16 | 11 | Patrick Croughwell | 17:04.9PR | CT | Norwich Free Academy | Sep 23
| 16th Ocean State XC Invitational |
| 18. | 15 | 10 | Brandon Brites | 17:08.9PR | CT | Danbury Hatters HCYS Track & XC Club | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 19. | 16 | 11 | John Disturco | 17:16.3PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 20. | 17 | 11 | Spencer Paine | 17:21.0 | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 21. | 15 | 10 | Harrison Sydor | 17:25.7PR | CT | Staples | Sep 27
| Staples, Trumbull, Westhill at New Canaan |
| 22. | 16 | 10 | Ryan Jordan | 17:32.4PR | CT | New Canaan Blazers | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 23. | 17 | 12 | Andrew Reed | 18:02.0PR | CT | New Canaan | Sep 27
| Staples, Trumbull, Westhill at New Canaan |
| | 16 | 11 | Gabriel Diamante | 18:02.0PR | CT | Woodland | Oct 28
| CIAC Division SS Boys Championship |
| 25. | 16 | 11 | Lucas Califano | 18:04.0 | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| 26. | 16 | 11 | Kaamil Badami | 18:09.0PR | CT | Wilton | Oct 18
| FCIAC Cross Country Championships |
| 27. | 15 | 10 | Reide Augustyn | 18:40.5PR | CT | Litchfield | Sep 30
| 64th Nonnewaug XC Invitational |
| 28. | 16 | - | Owen Pothier | 18:45.2PR | CT | Quinebaug Valley Track Club | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 29. | 18 | 12 | Michael Fico | 18:49.8PR | CT | New Canaan | Sep 27
| Staples, Trumbull, Westhill at New Canaan |
| 30. | 15 | 10 | Josh Martin | 18:57.1PR | CT | Rockville | Sep 23
| 16th Ocean State XC Invitational |
| 31. | 16 | 11 | Luke Pesce | 19:13.7PR | CT | Litchfield | Sep 30
| 64th Nonnewaug XC Invitational |
| 32. | 15 | 10 | Cormac Kilkenny | 19:50.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 33. | 15 | 10 | Jessie Singleton Jr... | 19:51.0PR | CT | Bloomfield | Oct 10
| Bloomfield @ Windsor |
| 34. | 15 | 10 | David Cuenca Goddar... | 20:26.0PR | CT | New Canaan | Oct 18
| FCIAC Cross Country Championships |
| 35. | 16 | 11 | Brock Newman | 20:30.0PR | CT | Norwalk | Oct 18
| FCIAC Cross Country Championships |
| 36. | 17 | 12 | Matthew Waldron | 20:38.0 | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
| 37. | 15 | 9 | Sawyer Christmann | 20:57.6PR | CT | New Haven Age Group | Nov 12
| USATF Connecticut Association Junior Olympic ... |
| 38. | 15 | 10 | Liam Gilson | 21:00.6PR | CT | New Haven Age Group | Oct 8
| USATF-NY Cross Country Series - Meet 2 |
| 39. | 16 | 11 | Ian St. Germain | 21:03.3PR | CT | Abbott Tech(Henry) | Oct 16
| CTC Cross Country Championships |
| 40. | 14 | 9 | Gavin Lippi | 21:09.9PR | CT | South Windsor | Oct 13
| 11th Harry Geraghty XC Invite |
| 41. | 14 | 9 | Daylin McKim | 23:05.0PR | CT | Bloomfield | Oct 10
| Bloomfield @ Windsor |
| 42. | 16 | 11 | Alexander Hannon | 24:48.0 | CT | Danbury | Oct 18
| FCIAC Cross Country Championships |
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