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| Winner of bracket based on total points after round robin play. |
Round of 16 - Saturday, September 14, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 292841 | HRSC | 10:00 AM | 8 | VAR 04B Nero | 6 | vs. | Beach FC 04B Black Puskas | 0 | | 292837 | Western Albemarle High School | 11:00 AM | 1 | SOCA 04 U16B Premier | 4 | vs. | LMVSC Boys U16 Red (2004) | 2 |
Quarter Final - Saturday, September 28, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 292844 | Long Bridge Park | 11:00 AM | 4 | Arlington 2004B Blue | 5 | vs. | SOCA 04 U16B Premier | 0 | | 292846 | Riverside High School | 01:00 PM | 2 | Loudoun 04B Black | 2
- 1PK
| vs. | VAR 04B Nero | 2 | | 292845 | FFC Park | 02:00 PM | 9 | PWSI Boys 2004 Red | 0 | vs. | Beach FC 04B Black Eusebio | 3 | | 292847 | EC Lawrence Park | 03:00 PM | 3 | SYA Cardinals 04B White | 2 | vs. | Virginia Legacy Wizards Green | 1 |
Semi-Final - Saturday, November 02, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 292849 | Publix Virginia Soccer Training Center | 11:00 AM | 1 | Loudoun 04B Black | 1 | vs. | SYA Cardinals 04B White | 0 | | 292848 | Publix Virginia Soccer Training Center | 03:00 PM | 1 | Arlington 2004B Blue | 0 | vs. | Beach FC 04B Black Eusebio | 2 |
Final - Sunday, November 03, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 292850 | Publix Virginia Soccer Training Center | 01:30 PM | 7 | Beach FC 04B Black Eusebio | 2 | vs. | Loudoun 04B Black | 3 |
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