| Round 1 24 boats |
|---|
| 1 |  | Annapolis High School Panthers | 3-4-6 | vs | 1-2-5 | Archbishop Spalding Cavaliers |  |
| 2 |  | Norfolk Collegiate School Oaks | 2-3-5 | vs | 1-4-6 | Norfolk Academy Bulldogs |  |
| 3 |  | Mercy High School Varsity | 4-5-6 | vs | 1-2-3 | Christchurch School Seahorses |  |
| 4 |  | Phoebus High School Phantoms | 1-5-6 | vs | 2-3-4 | Southern Regional High School Rams |  |
| 5 |  | Key School Zags | 1-3-5 | vs | 2-4-6 | Annapolis High School Panthers | |
| 6 | | Norfolk Academy Bulldogs | 1-3-4 | vs | 2-5-6 | Severn School Admirals |  |
| 7 | | Archbishop Spalding Cavaliers | 1-2-6 | vs | 3-4-5 | Mercy High School Varsity | |
| 8 | | Southern Regional High School Rams | 3-5-6 | vs | 1-2-4 | Norfolk Collegiate School Oaks | |
| 9 | | Christchurch School Seahorses | 1-2-4 | vs | 3-5-6 | Key School Zags | |
| 10 | | Severn School Admirals | 1-2-5 | vs | 3-4-6 | Phoebus High School Phantoms | |
| 11 | | Mercy High School Varsity | 1-5-6 | vs | 2-3-4 | Annapolis High School Panthers | |
| 12 | | Norfolk Academy Bulldogs | 2-3-6 | vs | 1-4-5 | Southern Regional High School Rams | |
| 13 | | Archbishop Spalding Cavaliers | 4-5-6 | vs | 1-2-3 | Key School Zags | |
| 14 | | Severn School Admirals | 1-2-5 | vs | 3-4-6 | Norfolk Collegiate School Oaks | |
| 15 | | Annapolis High School Panthers | 3-4-5 | vs | 1-2-6 | Christchurch School Seahorses | |
| 16 | | Phoebus High School Phantoms | 4-5-6 | vs | 1-2-3 | Norfolk Academy Bulldogs | |
| 17 | | Key School Zags | 1-2-4 | vs | 3-5-6 | Mercy High School Varsity | |
| 18 | | Southern Regional High School Rams | 2-3-6 | vs | 1-4-5 | Severn School Admirals | |
| 19 | | Christchurch School Seahorses | 2-3-4 | vs | 1-5-6 | Archbishop Spalding Cavaliers | |
| 20 | | Norfolk Collegiate School Oaks | 1-2-4 | vs | 3-5-6 | Phoebus High School Phantoms | |
| 21 | | Annapolis High School Panthers | 3-4-5 | vs | 1-2-6 | Norfolk Academy Bulldogs | |
| 22 | | Key School Zags | 1-2-4 | vs | 3-5-6 | Southern Regional High School Rams | |
| 23 | | Mercy High School Varsity | 3-4-5 | vs | 1-2-6 | Severn School Admirals | |
| 24 | | Christchurch School Seahorses | 1-2-5 | vs | 3-4-6 | Phoebus High School Phantoms | |
| 25 | | Archbishop Spalding Cavaliers | 1-2-4 | vs | 3-5-6 | Norfolk Collegiate School Oaks | |
| 26 | | Annapolis High School Panthers | 1-2-4 | vs | 3-5-6 | Southern Regional High School Rams | |
| 27 | | Key School Zags | 1-4-5 | vs | 2-3-6 | Norfolk Academy Bulldogs | |
| 28 | | Christchurch School Seahorses | 1-2-5 | vs | 3-4-6 | Severn School Admirals | |
| 29 | | Mercy High School Varsity | 1-3-5 | vs | 2-4-6 | Phoebus High School Phantoms | |
| 30 | | Archbishop Spalding Cavaliers | 3-4-5 | vs | 1-2-6 | Southern Regional High School Rams | |
| 31 | | Annapolis High School Panthers | 3-4-5 | vs | 1-2-6 | Norfolk Collegiate School Oaks | |
| 32 | | Key School Zags | 3-4-5 | vs | 1-2-6 | Severn School Admirals | |
| 33 | | Norfolk Academy Bulldogs | 1-2-4 | vs | 3-5-6 | Mercy High School Varsity | |
| 34 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | Phoebus High School Phantoms | |
| 35 | | Christchurch School Seahorses | 1-4-5 | vs | 2-3-6 | Norfolk Collegiate School Oaks | |
| 36 | | Annapolis High School Panthers | 2-3-6 | vs | 1-4-5 | Severn School Admirals | |
| 37 | | Southern Regional High School Rams | 1-3-4 | vs | 2-5-6 | Mercy High School Varsity | |
| 38 | | Key School Zags | 1-2-5 | vs | 3-4-6 | Phoebus High School Phantoms | |
| 39 | | Norfolk Academy Bulldogs | 2-3-4 | vs | 1-5-6 | Christchurch School Seahorses | |
| 40 | | Archbishop Spalding Cavaliers | 2-4-6 | vs | 1-3-5 | Severn School Admirals | |
| 41 | | Mercy High School Varsity | 3-4-6 | vs | 1-2-5 | Norfolk Collegiate School Oaks | |
| 42 | | Annapolis High School Panthers | 1-2-5 | vs | 3-4-6 | Phoebus High School Phantoms | |
| 43 | | Christchurch School Seahorses | 1-2-6 | vs | 3-4-5 | Southern Regional High School Rams | |
| 44 | | Norfolk Academy Bulldogs | 3-4-5 | vs | 1-2-6 | Archbishop Spalding Cavaliers | |
| 45 | | Key School Zags | 1-5-6 | vs | 2-3-4 | Norfolk Collegiate School Oaks | |
