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.
Fleming Island vs. Middleburg
| Series Record |
|---|
| Fleming Island leads series 16-2 |
| Date/Season | Level | Matchup | Winner | Score | Location | Type |
|---|---|---|---|---|---|---|
| Oct 16, 2026 | 11-Man | Middleburg at Fleming Island | — | Scheduled | Randy Warren Stadium | Regular Season |
| Oct 24, 2025 | 11-Man | Middleburg at Fleming Island | Fleming Island | 21-10 | Randy Warren Stadium | Regular Season |
| Oct 25, 2024 | 11-Man | Fleming Island at Middleburg | Fleming Island | 42-6 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 7, 2018 | 11-Man | Fleming Island at Middleburg | Fleming Island | 35-14 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 8, 2017 | 11-Man | Fleming Island at Middleburg | Fleming Island | 27-6 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 9, 2016 | 11-Man | Fleming Island at Middleburg | Fleming Island | 3-0 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 11, 2015 | 11-Man | Middleburg at Fleming Island | Fleming Island | 28-7 | Randy Warren Stadium | Regular Season |
| Sep 12, 2014 | 11-Man | Fleming Island at Middleburg | Fleming Island | 42-6 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 13, 2013 | 11-Man | Middleburg at Fleming Island | Fleming Island | 61-0 | Randy Warren Stadium | Regular Season |
| Sep 14, 2012 | 11-Man | Middleburg at Fleming Island | Fleming Island | 42-0 | Randy Warren Stadium | Regular Season |
| Sep 16, 2011 | 11-Man | Fleming Island at Middleburg | Fleming Island | 43-0 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Oct 29, 2010 | 11-Man | Middleburg at Fleming Island | Fleming Island | 37-0 | Randy Warren Stadium | Regular Season |
| Oct 30, 2009 | 11-Man | Fleming Island at Middleburg | Middleburg | 25-24 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Sep 4, 2008 | 11-Man | Middleburg at Fleming Island | Fleming Island | 31-6 | Randy Warren Stadium | Regular Season |
| Aug 31, 2007 | 11-Man | Fleming Island at Middleburg | Fleming Island | 41-23 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Oct 19, 2006 | 11-Man | Middleburg at Fleming Island | Fleming Island | 49-8 | Randy Warren Stadium | Regular Season |
| Oct 21, 2005 | 11-Man | Fleming Island at Middleburg | Fleming Island | 34-28 | Alan Powers Field at Garber Automall Stadium | Regular Season |
| Oct 1, 2004 | 11-Man | Middleburg at Fleming Island | Fleming Island | 19-6 | Randy Warren Stadium | Regular Season |
| Oct 3, 2003 | 11-Man | Fleming Island at Middleburg | Middleburg | 40-10 | Alan Powers Field at Garber Automall Stadium | Regular Season |
