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| Advancing to Next Round: top 4 place team(s) from each Bracket and 0 Wildcards. |
Bracket - Sunday, March 24, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 862981 | Pepsi Yuengling | 01:00 PM | 1 | A4 vs A2 | Black Watch FC | 1 | vs. | SFC United 2 | 3 |
Bracket - Sunday, April 07, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 862983 | Oscar Cooler | 09:00 AM | 1 | A6 vs A7 | Lutz Rangers | 3 | vs. | San Juan Bosco FC | 0 | | 862980 | Fruitville | 11:00 AM | 1 | A1 vs A3 | SFC FA Euro Sassari | 0 | vs. | SFC United 1 | 3 | | 862982 | Puryear Park | 01:00 PM | 5 | A5 vs A8 | SPFC Aztecs Second | 1 | vs. | Brandon Town FC Second | 3 |
Bracket - Sunday, June 02, 2019| Game | Venue | Time | Field | Group | Home Team | Score | | Away Team | Score | | 50052 | Fruitville | 11:00 AM | 1 | A3 vs A2 | SFC United 1 | 3 | vs. | SFC United 2 | 2 | | 50053 | Shimberg | 11:00 AM | 1 | A6 vs A8 | Lutz Rangers | 0 | vs. | Brandon Town FC Second | 4 |
Final - Sunday, June 23, 2019| Game | Venue | Time | Field | Home Team | Score | | Away Team | Score | | 67798 | Fruitville | 09:00 AM | 1 | Brandon Town FC Second | | vs. | SFC United 2 | |
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