| Saturday, May 29, 2021 | |
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| 12:02 AM* | - | 0 | Aspen Hill 05 Elite | | | | Boys U16 Virginia Cup 0 | |
3 | DC UNITED ACADEMY 2006 | | |
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| 12:02 AM* | - | 3 | DC UNITED ACADEMY 2006 | | | | Boys U16 Virginia Cup 0 | |
1 | Doradus Sdor 05 Elite | | |
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| 12:02 AM* | - | 1 | Doradus Sdor 05 Elite | | | | Boys U16 Virginia Cup 0 | |
1 | Aspen Hill 05 Elite | | |
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| 12:02 AM* | - | 0 | Syc 2005 Boys Blue | | | | Boys U16 Virginia Cup 0 | |
1 | DORADUS SDOR 05 PREMIER | | |
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| 12:02 AM* | - | 3 | LOUDOUN SOCCER 05B BLACK | | | | Boys U16 Virginia Cup 0 | |
1 | Syc 2005 Boys Blue | | |
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| 12:02 AM* | - | 1 | DORADUS SDOR 05 PREMIER | | | | Boys U16 Virginia Cup 0 | |
0 | Loudoun Soccer 05b Black | | |
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| Sunday, May 30, 2021 | |
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| 12:02 AM* Semi Final | - | 5 | DC UNITED ACADEMY 2006 | | | | Boys U16 Virginia Cup 0 | |
0 | Loudoun Soccer 05b Black | | |
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| 12:02 AM* Semi Final | - | 0 | Doradus SDor 05 Premier | | | | Boys U16 Virginia Cup 0 | |
1 | DORADUS SDOR 05 ELITE | | |
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| 12:02 AM* Cons. | - | 0 | Aspen Hill 05 Elite | | | | Boys U16 Virginia Cup 0 | |
7 | SYC 2005 BOYS BLUE | | |
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| Monday, May 31, 2021 | |
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| 12:02 AM* Final | - | 4 | DC UNITED ACADEMY 2006 | | | | Boys U16 Virginia Cup 0 | |
0 | Doradus Sdor 05 Elite | | |
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