Freeport Football Heartbreakers


As long-time DeFuniak Springs sports guru Sonny Yates used to exclaim, “You can smell it in the air!” as we enter the final week of July, we are now under a month away from the start of football season and it can’t get here soon enough! Over the last couple of weeks I’ve entertained myself (and hopefully somebody else out there who reads The DeFuniak Herald/Beach Breeze) by listing what I believe to be the top five biggest football wins in the history of Freeport and South Walton High School. I keep harassing Sports Editor Pat Casey to do a Walton list, but to be fair, Walton has a whole century worth of games to go through while Freeport has only 41 years worth and South Walton 14. Additionally, Pat uses a lot of his summer to get ready for the Walton High Sports Hall of Fame ceremony and write up while also working on his extensive archive collection and other sports related projects for the paper. Me? I just do things like ponder what I think are the top five most heartbreaking losses in Freeport football history. Here’s my list:
Three way tie: Freeport, in the span of four weeks beginning on Sept. 18, 1987, lost at Jay 15-7 in overtime, at Baker 21-19 and at home to Graceville 7-6.
Legendary Florida Panhandle coach Jeff Webb led Freeport to its first winning record in 1987 with a 7-3 mark. Yet, it’s astonishing to imagine just how good the Bulldog’s record could have been had Webb’s scrappy bunch been better at executing extra points. In the 1980’s, there were no two area rural football programs more proud than Graceville, who was a year away from winning the 1988 state title, and Baker, who played in four state championship games during the decade, winning three. The Bulldogs matched each of those teams touchdown for touchdown, but faulty kicking helped cause the mix-and-matched jersey-clad 1987 team to lose both of those contests by a combined three points. Jay, a renowned program in their own right at the time, defeated the visitors from Walton County in a 15-7 overtime nail-biter.
Jay 29, Freeport 22: On Oct. 25, 2002, Freeport fans packed Bulldog Stadium in hopes of watching the hometown squad win their first league championship in school history as the Bulldogs hosted Jay in a de facto district championship game. However, in a battle of 7-1 teams, the visiting Royals stayed one step ahead of Jim Anderson’s crew the entire contest and used a fake punt in the final quarter to prolong a scoring drive that, ultimately, sealed the game. It would be another seven years before Freeport would finally win their first district championship.
Vernon 23, Freeport 21: For the second year in a row, Freeport found themselves on the heartbreaking end of a de facto district championship game, this time, at the hands of a Jeff Webb coached Vernon team that was kick-starting a noteworthy run of success. Bulldog quarterback Josh Mckay scored two touchdowns against the Yellow Jackets, but if you ask many of the faithful in attendance, they will proclaim that the star quarterback actually crossed the goal line on a late drive that should have given the Bulldogs the lead only to have Mckay ruled short by the officials. Additionally, a field goal attempt on a fourth down of that drive was narrowly missed (or made), but ruled wide, depending on who you talk to.
Northview 34, Freeport 28 in Class A Regional Championship in 2012: Current head football coach Shaun Arntz, who was then the team’s Defensive Coordinator, called it ‘the most heartbreaking loss he’s ever been associated with’. On Nov. 23, 2012, Freeport traveled to northern Escambia County for a match-up against a powerful Northview squad that was looking to advance to the Final Four for the third consecutive year and that had already blasted the Bulldogs 42-0 in the regular season. This time, however, Freeport coach Jim Anderson used his entire arsenal, catching his heavily favored opponent off guard, to send the game into overtime with both teams tied at 28-all. What originally seemed an impossible chance at victory turned probable when running back Owen Cole appeared to score a 10-yard touchdown run on the first play of overtime. However, after a frivolous holding call negated the score, the Bulldogs would eventually turn the ball over on downs and Northview would score on their second offensive play to escape with a 34-28 win. The Chiefs would go on to win the Class A state championship.
Walton 27, Freeport 21: On Oct 21, 1995, an unimpressive Freeport squad with a 1-4 record hosted heavily favored Walton at the old varsity football stadium located on Kylea Laird Drive. It was a highly anticipated match-up between two intra-county schools that had not played each other in fifteen years and only three times overall. The home side of the overflow crowd was sent into a frenzy when running back David Porter gave coach Tripp Hope’s squad a 21-20 lead with 2:28 remaining following a 5-yard touchdown run and two- point conversion. However, Walton answered on the subsequent drive when Kendell Nelson connected with a leaping Markey Holmes for a 28-yard touchdown in the final minute to steal the victory.