| Date | Time | Sport | Opponent | Level | Game Type |
| 08/20/2019 | 03:30PM | Golf, Boys | East Lee County | Varsity | Non-District |
| 08/20/2019 | 03:30PM | Golf, Girls | @East Lee County | Varsity | Non-District |
| 08/20/2019 | 07:00PM | Volleyball, Girls | Dunbar | Varsity | District |
| 08/20/2019 | 06:00PM | Volleyball, Girls | Dunbar | Junior Varsity | Non-District |
| 08/22/2019 | 03:30PM | Golf, Girls | Estero | Varsity | Non-District |
| 08/22/2019 | 03:30PM | Golf, Boys | @Estero | Varsity | Non-District |
| 08/22/2019 | 07:00PM | Volleyball, Girls | Estero | Varsity | Non-District |
| 08/22/2019 | 06:00PM | Volleyball, Girls | Estero | Junior Varsity | Non-District |
| 08/27/2019 | 03:30PM | Golf, Boys | Fort Myers | Varsity | Non-District |
| 08/27/2019 | 03:30PM | Golf, Girls | @Fort Myers | Varsity | Non-District |
| 08/27/2019 | 03:00PM | Bowling, Boys | @North Fort Myers | Varsity | District |
| 08/27/2019 | 03:00PM | Bowling, Girls | @North Fort Myers | Varsity | District |
| 08/27/2019 | 07:00PM | Volleyball, Girls | North Fort Myers | Varsity | District |
| 08/27/2019 | 06:00PM | Volleyball, Girls | North Fort Myers | Junior Varsity | Non-District |
| 08/29/2019 | 03:30PM | Golf, Girls | Ida Baker | Varsity | Non-District |
| 08/29/2019 | 05:30PM | Volleyball, Girls | @Ida Baker | Junior Varsity | Non-District |
| 08/29/2019 | 06:30PM | Volleyball, Girls | @Ida Baker | Varsity | Non-District |
| 08/29/2019 | 03:00PM | Golf, Boys | @Ida Baker | Varsity | Non-District |
| 08/29/2019 | 03:00PM | Bowling, Boys | East Lee County | Varsity | Non-District |
| 08/29/2019 | 03:00PM | Bowling, Girls | East Lee County | Varsity | Non-District |
| 08/29/2019 | 06:30PM | Football (11 man) | @Estero | Junior Varsity | Non-District |
| 08/30/2019 | 07:00PM | Football (11 man) | @North Fort Myers | Varsity | Non-District |
| 09/03/2019 | 03:30PM | Golf, Boys | Island Coast | Varsity | Non-District |
| 09/03/2019 | 03:30PM | Bowling, Boys | @Cape Coral | Varsity | Non-District |
| 09/03/2019 | 03:30PM | Bowling, Girls | @Cape Coral | Varsity | Non-District |
| 09/03/2019 | 03:30PM | Golf, Girls | @Island Coast | Varsity | Non-District |
| 09/05/2019 | 03:30PM | Golf, Girls | Lehigh | Varsity | Non-District |
| 09/05/2019 | 03:30PM | Golf, Boys | @Lehigh | Varsity | Non-District |
| 09/05/2019 | 06:00PM | Swimming, Boys | @North Fort Myers | Varsity | Non-District |
| 09/05/2019 | 06:00PM | Swimming, Girls | @North Fort Myers | Varsity | Non-District |
| 09/05/2019 | 07:00PM | Volleyball, Girls | Barron Collier | Varsity | Non-District |
| 09/05/2019 | 03:00PM | Bowling, Boys | @Bishop Verot | Varsity | Non-District |
| 09/05/2019 | 03:00PM | Bowling, Girls | @Bishop Verot | Varsity | Non-District |
| 09/05/2019 | 05:30PM | Volleyball, Girls | Barron Collier | Junior Varsity | Non-District |
| 09/06/2019 | 07:00PM | Football (11 man) | Charlotte | Varsity | Non-District |
| 09/10/2019 | 06:00PM | Swimming, Boys | Cypress Lake | Varsity | Non-District |
| 09/10/2019 | 03:30PM | Golf, Boys | Mariner | Varsity | Non-District |
| 09/10/2019 | 06:00PM | Swimming, Girls | Cypress Lake | Varsity | Non-District |
| 09/10/2019 | 03:30PM | Golf, Girls | @Mariner | Varsity | Non-District |
| 09/10/2019 | 03:00PM | Bowling, Boys | Bonita Springs | Varsity | Non-District |
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