| Date | Flight | Home Team | Flight | Visitors |
| 4/2/2023 | U10 boy A | Darien Soccer - B2013 Blue | U10 boy b1 | Ridgefield U10 Boys BLK |
| 4/2/2023 | U10 Girls A | Newtown Soccer Club U10 - G2013 BLUE | U10 Girls B1 | Danbury 2013 U10 girls |
| 4/2/2023 | U13 Boys B | Monroe Soccer Club Boys U13 | U13 Boys A | B.13.10.S23.SCNM.Arsenal New Milford |
| 4/2/2023 | U15 Girls C | Bethel G2008 (1/1-B/C) | U15 Girls B | Shelton FC 2009 Girls Black F22/S23 |
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| 4/16/2023 | U10 boy A | OGRCC 2013 Thunder Blue | U10 boy b1 | BU10 Easton Redding B2013 Gold (1/1-B) |
| 4/16/2023 | U10 Girls B1 | Greenwich Blaze G13 | U10 Girls A | OGRCC 2013 Thunder Blue |
| 4/16/2023 | U13 Boys B | Norwalk Junior - B2010 | U13 Boys A | Darien Soccer - B2010 Blue |
| 4/16/2023 | U15 Girls B | Stamford FC U14/U13 Girls (2008/2009 | U15 Girls C | TUSC U13/14G Extreme |
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| 4/23/2023 | U10 boy b1 | Wilton B2013 Real | U10 boy A | New Canaan FC 2013 (U10) Boys Red |
| 4/23/2023 | U10 Girls A | New Canaan FC Red 2013 U10 Girls Red | U10 Girls B1 | OGRCC 2013 Thunder White |
| 4/23/2023 | U13 Boys B | Newtown Soccer Club U13 - B2010 | U13 Boys A | Norwalk CSC - B U13 |
| 4/23/2023 | U15 Girls C | Darien Soccer - G2008/09 White | U15 Girls B | Wilton G2008/09 Blue |
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| 4/30/2023 | U10 boy b1 | Ridgefield U10 Boys BLK | U10 boy A | WESTPORT U10 (2013) Boys Blue |
| 4/30/2023 | U10 Girls A | WESTPORT U10 (2013) GIRLS BLUE | U10 Girls B1 | Shelton FC 2013 Girls Black F22/S23 |
| 4/30/2023 | U13 Boys B | BU13 Gold Easton Redding B2010 Gold (1/2-E) | U13 Boys A | New Canaan FC 2010 (U13) Boys Red |
| 4/30/2023 | U15 Girls C | Norwalk Junior - G09/08 | U15 Girls B | FUSA U15G Red |
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| 5/7/2023 | U10 boy A | FUSA U10B Black | U10 boy b1 | Norwalk CSC - B U10 |
| 5/7/2023 | U10 Girls B1 | Darien Soccer - G2013 White | U10 Girls A | Darien Soccer - G2013 Blue |
| 5/7/2023 | U13 Boys A | Ridgefield U13 Boys BLK | U13 Boys B | Stamford FC U13 Boys White (2010) |
| 5/7/2023 | U15 Girls B | New Canaan FC 0809 (U15) Girls Red | U15 Girls C | FUSA U15G White |
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| 5/14/2023 | U10 boy b1 | Darien Soccer - B2013 White | U10 boy A | Darien Soccer - B2013 Blue |
| 5/14/2023 | U10 Girls A | Stamford FC U10 Girls - (2013) | U10 Girls B1 | Danbury 2013 U10 girls |
| 5/14/2023 | U13 Boys B | Bethel B2010 (1/1-B) | U13 Boys A | B.13.10.S23.SCNM.Arsenal |
| 5/14/2023 | U15 Girls C | Bethel G2008 (1/1-B/C) | U15 Girls B | Shelton FC 2009 Girls Black F22/S23 |
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| 5/21/2023 | U10 boy b1 | Weston B2013 Blue | U10 boy A | WESTPORT U10 (2013) Boys Blue |
| 5/21/2023 | U10 Girls A | FUSA U10G Black | U10 Girls B1 | Greenwich Blaze G13 |
| 5/21/2023 | U13 Boys A | New Canaan FC 2010 (U13) Boys Red | U13 Boys B | WESTPORT U13 (2010) BOYS BLUE |
| 5/21/2023 | U15 Girls B | FUSA U15G Red | U15 Girls C | Norwalk Junior - G09/08 |
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| 6/4/2023 | U10 boy A | New Canaan FC 2013 (U10) Boys Red | U10 boy b1 | Shelton FC 2013 Boys Black F22/S23 |
| 6/4/2023 | U10 Girls B1 | OGRCC 2013 Thunder White | U10 Girls A | Newtown Soccer Club U10 - G2013 BLUE |
| 6/4/2023 | U13 Boys B | Monroe Soccer Club Boys U13 | U13 Boys A | Norwalk CSC - B U13 |
| 6/4/2023 | U15 Girls C | Darien Soccer - G2008/09 White | U15 Girls B | Wilton G2008/09 Blue |