Series History & Rivalry Matchups
Welcome to the Head-to-Head database — your deep dive into Florida high school football history. Explore past matchups between any two teams, track series records, revisit classic games, and see how rivalries have evolved over time.
This is an ongoing project as we continue to build on decades of results across the state. Some series may be incomplete, but new games, scores, and historical details are being added regularly.
Dive in, explore, and don’t be surprised if you lose track of time — there’s a lot of history here.
To reset the page fully, click here.
Head-to-Head Series
Select two teams to view their series history.
Naples vs. Cypress Lake (Fort Myers)
| Series Record |
|---|
| Naples leads series 17-13 |
| Date/Season | Level | Winner | Score | Location | Type |
|---|---|---|---|---|---|
| Oct 1, 2010 | 11-Man | Naples | 44-21 | Thomas Broomhead Stadium | Regular Season |
| Oct 2, 2009 | 11-Man | Naples | 42-0 | Staver Field | Regular Season |
| Nov 5, 2004 | 11-Man | Naples | 50-7 | Thomas Broomhead Stadium | Regular Season |
| Nov 7, 2003 | 11-Man | Naples | 63-0 | Staver Field | Regular Season |
| Sep 26, 1998 | 11-Man | Cypress Lake (Fort Myers) | 14-0 | Thomas Broomhead Stadium | Regular Season |
| Sep 26, 1997 | 11-Man | Naples | 21-7 | Thomas Broomhead Stadium | Regular Season |
| Oct 23, 1992 | 11-Man | Cypress Lake (Fort Myers) | 35-8 | Staver Field | Regular Season |
| Oct 25, 1991 | 11-Man | Cypress Lake (Fort Myers) | 20-0 | Thomas Broomhead Stadium | Regular Season |
| Oct 9, 1987 | 11-Man | Cypress Lake (Fort Myers) | 17-6 | Thomas Broomhead Stadium | Regular Season |
| Oct 3, 1986 | 11-Man | Cypress Lake (Fort Myers) | 9-7 | Staver Field | Regular Season |
| Nov 2, 1984 | 11-Man | Naples | 17-6 | Staver Field | Regular Season |
| Nov 4, 1983 | 11-Man | Cypress Lake (Fort Myers) | 21-3 | Thomas Broomhead Stadium | Regular Season |
| Nov 5, 1982 | 11-Man | Naples | 20-14 | Staver Field | Regular Season |
| Nov 6, 1981 | 11-Man | Naples | 44-20 | Thomas Broomhead Stadium | Regular Season |
| Nov 7, 1980 | 11-Man | Cypress Lake (Fort Myers) | 21-20 | Staver Field | Regular Season |
| Nov 2, 1979 | 11-Man | Naples | 38-14 | Thomas Broomhead Stadium | Regular Season |
| Nov 3, 1978 | 11-Man | Cypress Lake (Fort Myers) | 34-0 | Staver Field | Regular Season |
| Nov 4, 1977 | 11-Man | Cypress Lake (Fort Myers) | 27-12 | Thomas Broomhead Stadium | Regular Season |
| Oct 22, 1976 | 11-Man | Naples | 42-19 | Staver Field | Regular Season |
| Oct 17, 1975 | 11-Man | Naples | 15-8 | Thomas Broomhead Stadium | Regular Season |
| Nov 9, 1974 | 11-Man | Naples | 20-13 | Staver Field | Regular Season |
| Oct 26, 1973 | 11-Man | Cypress Lake (Fort Myers) | 20-12 | Thomas Broomhead Stadium | Regular Season |
| Oct 27, 1972 | 11-Man | Naples | 8-6 | Staver Field | Regular Season |
| Oct 29, 1971 | 11-Man | Naples | 14-0 | Thomas Broomhead Stadium | Regular Season |
| Oct 30, 1970 | 11-Man | Cypress Lake (Fort Myers) | 42-6 | Staver Field | Regular Season |
| Oct 31, 1969 | 11-Man | Cypress Lake (Fort Myers) | 12-7 | Thomas Broomhead Stadium | Regular Season |
| Nov 1, 1968 | 11-Man | Naples | 43-14 | Staver Field | Regular Season |
| Oct 27, 1967 | 11-Man | Naples | 29-0 | Thomas Broomhead Stadium | Regular Season |
| Oct 28, 1966 | 11-Man | Cypress Lake (Fort Myers) | 12-6 | Staver Field | Regular Season |
| Oct 29, 1965 | 11-Man | Naples | 22-0 | Thomas Broomhead Stadium | Regular Season |
