| 100 Meters |
| 1. | 12 | | Jacquari Hayes | 11.70 | Apr 1 | Ram Country Invitational |
| 2. | 11 | | Bryson Waits | 11.77PR | Apr 29 | Apple Blossom Invitational |
| 3. | 11 | | Aaron Banks | 11.84cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 4. | 9 | | Jabril Hayes | 12.14c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | 12 | | Andrew Jefferies | 12.15 | May 12 | Millbrook Last Chance |
| 6. | 10 | | T.J. Washington | 12.16PR | Mar 22 | Strasburg Meet # 1 |
| 7. | 9 | | Luke Waits | 12.44cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 8. | 9 | | David Rivas | 12.54c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 9 | | Dakota Fitzwater | 12.54cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 10. | 10 | | Malachi Doleman | 12.69PR | Mar 22 | Strasburg Meet # 1 |
| 11. | - | | Tony Ross | 13.14cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 200 Meters |
| 1. | 12 | | Jacquari Hayes | 23.17PR | Apr 29 | Apple Blossom Invitational |
| 2. | 12 | | Andrew Jefferies | 23.88PR | May 18 | VHSL Conference 21 |
| 3. | 12 | | Kyle Holliday | 24.27PR | May 12 | Millbrook Last Chance |
| 4. | 10 | | T.J. Washington | 24.48PR | Mar 22 | Strasburg Meet # 1 |
| 5. | 9 | | Luke Waits | 25.74cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 6. | - | | Tony Ross | 28.54cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 400 Meters |
| 1. | 9 | | Ty Waits | 52.59 | Apr 29 | Apple Blossom Invitational |
| 2. | 10 | | Michael Diamantis | 53.59PR | May 18 | VHSL Conference 21 |
| 3. | 12 | | David Restrepo | 53.94 | May 12 | Millbrook Last Chance |
| 4. | 10 | | Erick Dotson | 55.23PR | Apr 1 | Ram Country Invitational |
| 5. | 12 | | Daniel Milburn | 55.44cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 6. | 10 | | Matthew Pilkington | 1:04.04cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 800 Meters |
| 1. | 10 | | Jacob Carr | 2:05.44PR | May 18 | VHSL Conference 21 |
| 2. | 12 | | Daniel Milburn | 2:07.31PR | Apr 22 | Lake Braddock Hall of Fame Invitational |
| 3. | 10 | | Lucas Williams | 2:12.32 | May 12 | Millbrook Last Chance |
| 4. | 11 | | John Arnold | 2:27.5hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | 9 | | Jacob Hammer | 2:28.0hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 6. | 9 | | Adam Brown | 2:31.6hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 7. | 12 | | Jacob Lewis | 2:33.6hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 8. | 10 | | Brenden Stoneberger | 2:34.6h | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 9. | 11 | | Tyler Hall | 2:52.9hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 1600 Meters |
| 1. | 11 | | Hayden Williams | 4:30.28PR | May 6 | Dogwood Classic |
| 2. | 10 | | Jacob Carr | 4:57.3hPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 3. | 10 | | Lucas Williams | 5:03.68 | Apr 22 | Lake Braddock Hall of Fame Invitational |
| |
| 3200 Meters |
| 1. | 11 | | Hayden Williams | 9:41.80PR | May 6 | Dogwood Classic |
| 2. | 10 | | Jacob Carr | 11:10.19PR | Mar 22 | Strasburg Meet # 1 |
| 3. | 10 | | Lucas Williams | 11:38.15PR | Mar 22 | Strasburg Meet # 1 |
| |
| 110m Hurdles - 39" |
| 1. | 12 | | Kyle Holliday | 15.83 | May 25 | 4A West Regional Outdoor T&F Championship |
| 2. | 12 | | David Restrepo | 16.11PR | May 25 | 4A West Regional Outdoor T&F Championship |
| 3. | 9 | | Riley O'Conner | 18.25 | May 18 | VHSL Conference 21 |
| 4. | 12 | | Caleb Byram | 19.24c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 300m Hurdles - 36" |
| 1. | 12 | | David Restrepo | 40.62PR | Apr 29 | Apple Blossom Invitational |
| 2. | 12 | | Kyle Holliday | 44.09 | Apr 29 | Apple Blossom Invitational |
| 3. | 9 | | Darius Lane | 47.70 | May 12 | Millbrook Last Chance |
| 4. | 12 | | Caleb Byram | 48.14cPR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | 9 | | Riley O'Conner | 48.84c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 4x100 Relay |
| 1. | | | T.J. Washington
Bryson Waits
Andrew Jefferies
Aaron Banks | 44.65 | Apr 29 | Apple Blossom Invitational |
| 2. | | | T.J. Washington
Bryson Waits
Aaron Banks
Andrew Jefferies | 44.83 | May 18 | VHSL Conference 21 |
| 3. | | | Relay Team | 44.86 | Apr 22 | Lake Braddock Hall of Fame Invitational |
| 4. | | | Aaron Banks
Bryson Waits
Andrew Jefferies
Jacquari Hayes | 45.14c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | | | T.J. Washington
Bryson Waits
Andrew Jefferies
Jabril Hayes | 45.50 | Apr 8 | Handley Invitational |
| 6. | | | T.J. Washington
Bryson Waits
Andrew Jefferies
David Rivas | 46.19 | Apr 1 | Ram Country Invitational |
| 7. | 9 | | David Rivas
Jabril Hayes
Dakota Fitzwater
Luke Waits | 48.55 | Mar 22 | Strasburg Meet # 1 |
| 8. | | | David Rivas
Jabril Hayes
Luke Waits
Tony Ross | 49.34c | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 4x400 Relay |
| 1. | | | David Restrepo
Ty Waits
Daniel Milburn
Michael Diamantis | 3:40.96 | Apr 8 | Handley Invitational |
| 2. | | | David Restrepo
Erick Dotson
Michael Diamantis
Ty Waits | 3:42.53 | Apr 1 | Ram Country Invitational |
| 3. | | | Relay Team | 3:43.53 | Apr 29 | Apple Blossom Invitational |
| 4. | | | Michael Diamantis
Ty Waits
Erick Dotson
Matthew Pilkington | 3:55.08 | Mar 22 | Strasburg Meet # 1 |
| 5. | | | Darius Lane
Erick Dotson
Jacob Hammer
John Arnold | 4:42.4h | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| 4x800 Relay |
| 1. | | | Relay Team | 8:46.38 | Apr 22 | Lake Braddock Hall of Fame Invitational |
| 2. | | | Jacob Carr
Hayden Williams
Lucas Williams
Daniel Milburn | 8:47.63 | Apr 1 | Ram Country Invitational |
| 3. | | | Daniel Milburn
Michael Diamantis
Jacob Carr
Lucas Williams | 8:49.18 | May 18 | VHSL Conference 21 |
| 4. | | | John Arnold
Jacob Hammer
Jacob Lewis
Brenden Stoneberger | 10:03.30 | Mar 22 | Strasburg Meet # 1 |
| |
| Shot Put - 12lb |
| 1. | 10 | | Isaiah Allen | 55' 6 | May 25 | 4A West Regional Outdoor T&F Championship |
| 2. | 12 | | Sam Johnson | 51' 0PR | May 18 | VHSL Conference 21 |
| 3. | 10 | | Daniel Bosespflug | 40' 10 | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 4. | - | | Nevin Schultz | 35' 5PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | 9 | | Henry Rusch | 25' 9PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| Discus - 1.6kg |
| 1. | 10 | | Isaiah Allen | 158' 0PR | Apr 22 | Lake Braddock Hall of Fame Invitational |
| 2. | 12 | | Sam Johnson | 140' 6PR | May 18 | VHSL Conference 21 |
| 3. | 10 | | Daniel Bosespflug | 102' 7 | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 4. | - | | Nevin Schultz | 60' 6PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 5. | 9 | | Henry Rusch | 59' 8PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| High Jump |
| 1. | 11 | | Bryson Waits | 5' 6PR | Apr 8 | Handley Invitational |
| 9 | | Jabril Hayes | 5' 6 | May 18 | VHSL Conference 21 |
| 3. | 9 | | David Rivas | 5' 4 | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| Long Jump |
| 1. | 10 | | T.J. Washington | 22' 3.25PR | May 25 | 4A West Regional Outdoor T&F Championship |
| 2. | 12 | | Jacquari Hayes | 22' 2.25PR | Mar 22 | Strasburg Meet # 1 |
| 3. | 11 | | Aaron Banks | 20' 1.5PR | May 18 | VHSL Conference 21 |
| 4. | 12 | | Andrew Jefferies | 19' 7PR | Mar 22 | Strasburg Meet # 1 |
| 5. | 9 | | Jabril Hayes | 18' 10.5 | Mar 22 | Strasburg Meet # 1 |
| 6. | 10 | | Malachi Doleman | 18' 1 | Mar 22 | Strasburg Meet # 1 |
| 7. | 9 | | Darius Lane | 16' 5.5 | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 8. | - | | Tony Ross | 14' 10.5PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
| Triple Jump |
| 1. | 10 | | T.J. Washington | 46' 1.25PR | Jun 3 | VHSL Group 4A State Championship |
| 2. | 12 | | Jacquari Hayes | 44' 0.5 | Apr 29 | Apple Blossom Invitational |
| 3. | - | | CJ Washington | 42' 3PR | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| 4. | 9 | | Jabril Hayes | 39' 9 | May 18 | VHSL Conference 21 |
| 5. | 9 | | Riley O'Conner | 37' 0PR | Mar 22 | Strasburg Meet # 1 |
| 6. | 9 | | Darius Lane | 36' 10.5 | Mar 22 | Strasburg Meet # 1 |
| 7. | 9 | | David Rivas | 35' 0PR | Mar 22 | Strasburg Meet # 1 |
| 8. | 11 | | Aaron Banks | 34' 9 | Apr 19 | Skyline vs. Sherando, Randolph-Macon Academy |
| |
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