Simon Kenton will bring one of northern Kentucky's most experienced rosters to Fort Mitchell on Aug. 21, when the Pioneers open the 2026 season at Dixie Heights at 7 p.m.

The Kenton County School District matchup pits two programs that both reached the 2025 playoffs. Simon Kenton won its first postseason game in three years, beating Oldham County 31-9 in the Class 6A first round before falling to two-time defending state champion Louisville Trinity. Dixie Heights lost a 52-49 shootout to Collins in the Class 5A first round, with quarterback Mason Fields throwing for 408 yards in that game.

Head coach Joe Wynn, entering year three at Simon Kenton, is 10-13 with the Pioneers and 64-40 in nine seasons overall. He told the NKY Tribune that last season's 6-6 finish exceeded expectations.

The Pioneers return seven offensive starters and six on defense. The headliner is junior quarterback Grant Webb, who stands 6-foot-5 and added 25 pounds of muscle in the offseason. As a sophomore, Webb threw for 1,810 yards and rushed for 309, totaling 2,119 combined yards. Wynn described him as a true dual-threat who can stretch the field 60-plus yards.

Webb will need new targets after the graduation of Grayson Harris, who piled up more than 3,100 receiving yards over three seasons.

Five junior wide receivers with varsity experience return, and senior Kyle King will pull double duty at tight end and linebacker. King recorded 40 tackles last fall, and fellow linebacker Jason Rabe led the team with 99. Together they anchor a defense that returns six starters, with seniors Jack Giordano and Jaxon Davis leading the secondary.

Seniors Cohen Endicott and Anthony Sparkman anchor the offensive line. Junior Mo Smith is the most experienced returning ball carrier.

The early schedule tests Simon Kenton before district play begins. After the Dixie Heights opener, the Pioneers travel to Covington Catholic on Sept. 4, and host Beechwood on Sept. 11. All three opponents rank among the toughest non-district matchups in northern Kentucky.

Simon Kenton competes in Class 6A, District 6 alongside Campbell County, Great Crossing, and Ryle. Winning the district would guarantee a home playoff game.

Kickoff at Dixie Heights is 7 p.m. on Aug. 21.