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- 09/06/2019, Calvert vs Leonardtown
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- 09/20/2019, Calvert vs Westlake (Gold Rush Game)
- 9/27/2019 Calvert vs Huntingtown (AAHG)
- 10/04/2019 Calvert at Lackey
- 10/11/2019 Calvert at Thomas Stone
- 10/18/2019 Calvert vs McDonough (Homecoming)
- 10/25/2019 Calvert vs Patuxent (Senior Night)
- 11/01/2019 Calvert at La Plata
- 11/08/2019 Calvert at Lackey (Round One of Play Offs)
- Calvert at Potomac (Round Two of Play Offs)
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