| Aug 24 (SAT) | ||
| Aug 31 | ||
| Sep 7 | Congress/Coaches’ Meeting | Hillsborough HS |
| Sep 14 (ACT) | ||
| Sep 21 | ||
| Sep 28 | FGCCFL All Events | Lakewood Ranch HS |
| Oct 5 (SAT) | ||
| Oct 12 | FGCCFL All Events | Southeast HS |
| Oct 19 | ||
| Oct 26 (ACT) | ||
| Nov 1-3 (SAT) | Blue Key weekend* | |
| Nov 9 | FGCCFL All Events | Strawberry Crest HS |
| Nov 16 | ||
| Nov 23 | ||
| Nov 30 | Thanksgiving | |
| Dec 7 (SAT) | ||
| Dec 14 (ACT) | NSDA District Congress | Pine View School |
| Dec 21 | Winter Break | |
| Dec 28 | Winter Break | |
| Jan 4 ’20 | ||
| Jan 11 | Sunvite weekend* | |
| Jan 18 | FGCCFL All Events | Sickles HS |
| Jan 25 | ||
| Feb 1 | FFL Regionals | Palm Harbor Univ HS |
| Feb 8 (ACT) | FGCCFL All Events | Durant HS |
| Feb 15 | Harvard weekend* | |
| Feb 21-22 | FGCCFL Grand Finals | Osceola HS |
| Feb 29-Mar 1 | FFL Varsity State | Olympia HS |
| Mar 7-8 | NSDA District Debate/IE | Wharton HS |
| Mar 14 (SAT) | Spring Break | |
| Mar 21 | Spring Break | |
| Mar 28 | ||
| Apr 4-5 (ACT) | FFL Novice State | Cypress Bay HS |
| May 2 (SAT) | ||
| May 23-24 | NCFL Grand Nationals | Chicago, IL |
| Jun 14-19 | NSDA Nationals | Albuquerque, NM |
* Starred tournaments are invitationals and are not connected with any league. They are included here as a courtesy.