Greenbrier reached the playoffs in all seven seasons from 1995 through 2001 under three head coaches. The 2002 team followed with the program's first TSSAA playoff victory.
Greenbrier reached the playoffs in every season from 1995 through 2001 while the program moved from Steve Sorrells to Scott Smith and then to Kirk Williams.
Greenbrier reaches November for a second straight year. A first-round rematch with Marshall County becomes Steve Sorrells's final game as head coach, closing the eight-season run that began in 1988.
People: The school records also preserves postseason honors for Trey Castleman, Thad Marcum and others, with a separate accolades record naming Chris Galbreath first-team All-State.
OPEN 1995 →A 0–3 opening gives way to a three-game winning streak and another playoff appearance. The streak included 9–6 wins over Spring Hill and DeKalb County.
People: Jeremiah Adams appears as All-Mid-State; Ray Riley, Rob Dorris, Chad Kennedy and Thad Marcum join him on the school’s All-Region 5-3A record.
OPEN 1996 →Smith's second team wins four games and reaches the first round at Chattanooga Brainerd. Brainerd won the first-round game 24–7.
People: B. J. Link, J. R. Somma, Eugene Raymer and Rob Dorris give the transition year a strong surviving Mid-State honors footprint.
OPEN 1997 →Kirk Williams takes over and Greenbrier wins four of five in the middle of the schedule. Howard won the first-round game 27–13.
People: Matthew Mayo, Roy Dill and B. J. Link are preserved as All-Mid-State selections as Kirk Williams takes over.
OPEN 1998 →The Bobcats finish 6–5, the program's first winning record since the 8–3 season of 1981.
People: Derek Adams and Stetson Dickerson are listed All-Mid-State; Adams also has a 155-yard rushing game against DeKalb in the Greenbrier records.
OPEN 1999 →Greenbrier starts 1–4, then beats Macon County, Springfield, Livingston Academy and DeKalb County in succession to secure Williams's third playoff trip in three seasons.
People: Stetson Dickerson is recorded as Region 4-3A Offensive MVP and J. B. Evans as the region’s Linebacker MVP.
OPEN 2000 →A 3–8 record still ends in the playoffs. All ten regular-season games are available on film, and a Giles County clipping documents the 48–20 late-season offensive surge that clinched another November berth.
People: The Region 5-3A records preserve four Greenbrier MVP awards: Curt Williams, Don Scott, Jonathon McDade and Bobby George.
OPEN 2001 →Greenbrier's head-coach records list the coaching dates for this period. A separate captain register records that seniors served as game captains from 1973 through 2001.
The transition ends with an 8–4 team, Greenbrier's first home TSSAA playoff game and a 27–0 win over Lexington for the program's first postseason victory.