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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 | | 290806 | Warhill | 01:00 PM | Turf 2 | Virginia Legacy Wizards Green | 2 | vs. | SOCA 05 U15B Premier | 0 | | 290801 | Greenbriar Park-Yorktown HS | 01:30 PM | 1 | Arlington 2005B White | 6 | vs. | LMVSC Boys U15 White (2005) | 0 | | 290800 | HRSC | 02:00 PM | 8 | Beach FC 05B Black Batistuta | 1 | vs. | Blue Ridge United 05B Orange | 0 | | 290802 | HRSC | 04:00 PM | 8 | VAR 05B Nero | 3 | vs. | VSA 05B PREMIER RED | 0 | | 290804 | Lewinsville Park | 04:00 PM | 3 | McLean 2005 Boys Green | 5 | vs. | Beach FC 05B Black Maradona | 0 |
Quarter Final - Saturday, October 05, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 290809 | Lewinsville Park | 12:00 PM | 2 | FCSC United 2005B Black | 0 | vs. | McLean 2005 Boys Green | 1 | | 290808 | Greenbriar Park-Yorktown HS | 12:15 PM | 1 | Arlington 2005B White | 1 | vs. | VAR 05B Nero | 0 | | 290810 | Hayfield High School | 01:00 PM | 1 | LMVSC Boys U15 Red (2005) | 2 | vs. | Virginia Legacy Wizards Green | 3 | | 290807 | Loudoun Soccer Park (LSP) | 03:00 PM | 1 | Loudoun 05B Black | 2 | vs. | Beach FC 05B Black Batistuta | 0 |
Semi-Final - Saturday, November 02, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 290811 | Publix Virginia Soccer Training Center | 01:00 PM | 5 | Loudoun 05B Black | 1 | vs. | Arlington 2005B White | 2 | | 290812 | Publix Virginia Soccer Training Center | 03:00 PM | 5 | McLean 2005 Boys Green | 3 | vs. | Virginia Legacy Wizards Green | 2 |
Final - Sunday, November 03, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 290813 | Publix Virginia Soccer Training Center | 11:30 AM | 7 | Arlington 2005B White | 1 | vs. | McLean 2005 Boys Green | 2 |
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