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| Advancing to Next Round: top 2 place team(s) from each Bracket and 0 Wildcards. |
Bracket - Saturday, November 02, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 316322 | Cascades Academy | 02:00 PM | 1 | D3 vs D1 | Bend FC Timbers 09B Red | 3 | vs. | Pacific FC B09 Rangers | 6 |
Bracket - Saturday, November 09, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 316323 | Wilson High School | 12:00 PM | TrfE | D2 vs D3 | FSC 09B Celtics White | 4 | vs. | Bend FC Timbers 09B Red | 2 |
Bracket - Sunday, November 10, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 316321 | Luke Jensen Sports Park | 12:00 PM | Trf4 | D1 vs D2 | Pacific FC B09 Rangers | 2 | vs. | FSC 09B Celtics White | 1 |
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