An intriguing first-round matchup is one that spans generations.

The 2001 Gators were the only Vicksburg High team this century to reach the 10-win mark. They entered the playoffs as a No. 3 seed in Region 2-5A, and then made a stirring run to the Class 5A semifinals before losing a close and high-scoring game to eventual state champ Starkville.

Their challenger comes from nearly a half-century earlier, but has the talent to match up with any team from any generation.

In an era of ground-and-pound offenses, the 1957 Culkin Wildcats took a far different approach. Quarterback Glynn Griffing — a Mississippi Sports Hall of Fame inductee for his later exploits at Ole Miss — and running back Walter Kinnebrew led a high-powered pass-heavy offense that averaged 31.7 points per game. The defense did not allow more than seven points to any opponent during a 9-0 season.

Griffing’s best season was 1956, when he threw 19 touchdown passes, and Culkin had another undefeated season in 1958. The 1957 team, however, hit on cylinders and is the representative for the school’s brief late 1950s dynasty.