| 04/06/2019 | Royals (CBB1) | Astros (CBB3) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 04/06/2019 | Astros (CBB3) | Pirates (CBB2) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 04/06/2019 | Pirates (CBB2) | Royals (CBB1) | 3:00PM - 5:00PM | CLL - Main Fields / Majors Field | |
| 04/08/2019 | OB3 | Royals (CBB1) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 04/08/2019 | Pirates (CBB2) | WIL1 | 6:00PM - 8:00PM | Wilson Little League / Wilson Major Field | |
| 04/10/2019 | CR1 | Astros (CBB3) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 04/22/2019 | BC1 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 04/22/2019 | Astros (CBB3) | BC2 | 6:00PM - 8:00PM | Bennetts Creek - Driver / Majors Field | |
| 04/22/2019 | Royals (CBB1) | CR1 | 6:00PM - 8:00PM | Cradock Little League Complex / Cradock Majors Field | |
| 04/27/2019 | BC2 | Royals (CBB1) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 04/27/2019 | BC4 | Astros (CBB3) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 04/27/2019 | Pirates (CBB2) | BC3 | 12:30PM - 2:30PM | Bennetts Creek - Driver / Majors Field | |
| 04/29/2019 | CLL1 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 04/29/2019 | Astros (CBB3) | CLL2 | 6:00PM - 8:00PM | Chesapeake Little League - Crestwood Park / Ches. Majors Field | |
| 05/01/2019 | BC4 | Royals (CBB1) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/04/2019 | CP4 | Astros (CBB3) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 05/04/2019 | Pirates (CBB2) | OB1 | 12:30PM - 2:30PM | Olive Branch Little League / OB Majors Field | |
| 05/04/2019 | Royals (CBB1) | CLL2 | 12:30PM - 2:30PM | Chesapeake Little League - Crestwood Park / Ches. Majors Field | |
| 05/06/2019 | Royals (CBB1) | CP4 | 6:00PM - 8:00PM | Charles Peete Little League / CP Major Field | |
| 05/08/2019 | CP3 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/08/2019 | Astros (CBB3) | CP2 | 6:00PM - 8:00PM | Charles Peete Little League / CP Major Field | |
| 05/11/2019 | CP2 | Royals (CBB1) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 05/11/2019 | CM1 | Astros (CBB3) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 05/11/2019 | Pirates (CBB2) | CP1 | 12:30PM - 2:30PM | Charles Peete Little League / CP Major Field | |
| 05/13/2019 | Astros (CBB3) | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/13/2019 | Royals (CBB1) | CM1 | 6:00PM - 8:00PM | Cavalier Manor LL / Major Field | |
| 05/18/2019 | OB2 | Astros (CBB3) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 05/18/2019 | Pirates (CBB2) | Royals (CBB1) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 05/20/2019 | OB3 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/20/2019 | Royals (CBB1) | OB2 | 6:00PM - 8:00PM | Olive Branch Little League / OB Majors Field | |
| 05/20/2019 | Astros (CBB3) | WIL1 | 6:00PM - 8:00PM | Wilson Little League / Wilson Major Field | |
| 05/21/2019 | BC1 | Astros (CBB3) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/22/2019 | WIL1 | Royals (CBB1) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/22/2019 | Pirates (CBB2) | CR1 | 6:00PM - 8:00PM | Cradock Little League Complex / Cradock Majors Field | |
| 05/28/2019 | BC2 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 05/28/2019 | Astros (CBB3) | BC3 | 6:00PM - 8:00PM | Bennetts Creek - Driver / Majors Field | |
| 05/29/2019 | Royals (CBB1) | BC1 | 6:00PM - 8:00PM | Bennetts Creek - Driver / Majors Field | |
| 06/01/2019 | CLL1 | Astros (CBB3) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 06/01/2019 | Pirates (CBB2) | BC4 | 10:00AM - 12:00PM | Bennetts Creek - Driver / Majors Field | |
| 06/01/2019 | CLL2 | Royals (CBB1) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 06/03/2019 | Royals (CBB1) | CLL1 | 6:00PM - 8:00PM | Chesapeake Little League - Crestwood Park / Ches. Majors Field | |
| 06/03/2019 | Astros (CBB3) | OB1 | 6:00PM - 8:00PM | Olive Branch Little League / OB Majors Field | |
| 06/05/2019 | CLL2 | Pirates (CBB2) | 6:00PM - 8:00PM | CLL - Main Fields / Majors Field | |
| 06/08/2019 | Astros (CBB3) | Royals (CBB1) | 10:00AM - 12:00PM | CLL - Main Fields / Majors Field | |
| 06/08/2019 | Royals (CBB1) | Pirates (CBB2) | 12:30PM - 2:30PM | CLL - Main Fields / Majors Field | |
| 06/08/2019 | Pirates (CBB2) | Astros (CBB3) | 3:00PM - 5:00PM | CLL - Main Fields / Majors Field | |