Alpharetta (GA) vs. Milton (GA)

Thursday, Aug. 29 at 7:30 PM ET

The event will begin with the latest chapter in the Milton-Alpharetta rivalry, as the defending state champion Eagles host the Raiders in a standalone game on Thursday night.

Milton emphatically announced its arrival on the national scene at the 2018 Freedom Bowl with a shellacking of highly-touted Cardinal Gibbons (FL), but head coach Adam Clack will be tasked with replacing Georgia Tech quarterback Jordan Yates.

That’s no small vacancy to fill, but the life of Yates’ heir apparent will be made easier by the return of Tchio to anchor the offensive line.

Pickerington Central (OH) vs. Winter Park (FL)

Friday, Aug. 30 at 5 PM ET

Friday begins with what figures to be one of the best matchups of the event, as Ohio powerhouse Pickerington Central meets Winter Park in the first game of a Freedom Bowl doubleheader.

Winter Park enjoyed a 10-2 campaign in 2018 before bowing out to eventual Florida state champion Mandarin. The Tigers’ ’18 season ended with a loss to Colerain in the semifinals.

Four-star cornerback Ethan Pouncey will lead a Wildcats defense looking to slow down a loaded Pickerington Central group headlined by Styles and three-star dual threat quarterback Demeatric Crenshaw.

Cocoa (FL) vs. Hoover (AL)

Friday, Aug. 30 at 8:30 PM ET

Arguably the premier game of the weekend will close us out on Friday, as Cocoa and Hoover battle in the first of two Florida-Alabama tilts.

Hoover, of course, needs no introduction, but here’s one anyway: Quarterback Robby Ashford is among the top signal callers in the 2020 class and he will lead a national powerhouse hungry for a rare bounce back season after only going 9-4 and losing to Thompson in the state semifinals a season ago. 

Caziah Holmes figures to line up at quarterback for Cocoa, but his position doesn’t tell the full story of his impact. Holmes is one of the most sought-after athletes in the country, with a who’s who list of suitors that includes Miami, Ohio State and Auburn, among others. Holmes recently clocked a 4.49 40-yard dash at The Opening regional.

Bishop Sycamore (OH) vs. Daytona Mainland (FL)

Saturday, Aug. 31 at 10:30 AM ET

Daytona Mainland makes its second trip to the Freedom Bowl in as many years after falling victim to a miracle comeback by Bob Jones (AL) in 2018.

The Buccaneers bounced back nicely after that defeat, winning seven of their next eight games before eventually falling to Northwestern in the 6A Florida state playoffs. Quarterback Taron Keith returns for his senior season after posting 1,169 total yards and eight touchdowns in ’18.

Sycamore enters 2019 hunting the playoff berth it narrowly missed a season ago. Head coach Scott Dattilo leads a young and talented roster into the second of two cross-country matchups between football rich states Ohio and Florida.

Clearwater Central Catholic (FL) vs. Brentwood Academy (TN)

Saturday, Aug. 31 at 2:30 PM ET

Brentwood Academy has long since established itself as a national powerhouse and one of the most disciplined teams in the country—an absolute credit to head coach Cody White and his staff.

The Eagles are balanced and strong, but calling them “balanced” is not meant to imply they’re barren of starpower, as three-star linebacker Devyn Curtis and four-star Eli Sutton are getting plenty of attention from top college programs—and rightfully so.

Of course, Curtis, Sutton & Co. will meet one of their most demanding challenges of the season in Clearwater Central Catholic, a program that went undefeated prior to a state title game loss to Chaminade Madonna in 2018—and has racked up 95 wins over the past nine seasons.

UMS-Wright (AL) vs. Western (FL)

Saturday, Aug. 31 at 7 PM ET

In 2018, the event’s grand finale between North Gwinnett and Wekiva lived up to expectations. A year later, founder David Menard and the good folks organizing the Freedom Bowl appear to have delivered once again.

Pitting UMS-Wright and Western in the Saturday night game puts an immense amount of talent on the field for what figures to be an electric final chapter of the 2019 Freedom Bowl.

The defending state champs from UMS-Wright feature one of Alabama’s top 2020 wide receiver prospects in Keyshawn Woodyard. Their opponents from Western reeled off wins in eight of nine last season—the lone loss, a three-point overtime setback at Miramar—before falling to Palm Beach Central in the second round of the 8A playoffs.