| Time | Date | Name | Meet |
|---|---|---|---|
| 49.99 | Feb. 15, 2020 | Clayton Whetstine | Virginia Independent School Championship (c) |
| 50.44 | Jan. 11, 2020 | Clayton Whetstine | Kecoughtan Invitational (c) |
| 51.33 | Feb. 16, 2019 | Clayton Whetstine | Virginia Independent School Championship (c) |
| 52.33 | Feb. 20, 2016 | Joey Kauffman | Virginia Independent School State Championship (c) |
| 53.82 | Feb. 13, 2016 | Joey Kauffman | TCIS Swimming Championship (c) |
| 54.66 | Feb. 6, 2016 | Joey Kauffman | Virginia LIS-VPL Championship (c) |
| 54.68 | Jan. 9, 2016 | Joey Kauffman | VA Kecoughtan Invitational (c) |
| 55.90 | Feb. 14, 2015 | Will Wilson | VA Independent School S&D Championship (c) |
| 56.78 | Feb. 23, 2013 | Jacob Kaskel | 13 Eastern Interscholastic Swimming Championships |
| 57.39 | Feb. 18, 2012 | Brandon Mueller | Virginia Independent High School Championships (c) |
| 57.86 | Feb. 19, 2011 | Brandon Mueller | Virginia Independent School Championship (c) |
| 59.42 | Feb. 14, 2009 | Evan Brush | Virginia Independent Schools Championship (c) |
| 1:00.37 | Feb. 7, 2009 | Evan Brush | VA TCIS Championship (c) |
| 1:03.65 | Jan. 10, 2009 | Evan Brush | VA Kecoughtan Invitational (c) |
| 1:03.74 | Feb. 23, 2008 | Evan Brush | Eastern Interscholastic Swimming Championship |
