1998
The 1998 Bluebirds team was considered the best team in all of Kentucky that year (they finished first in the state, regardless of classification, according to the state's ranking services), and in fact was considered by many to be the finest Kentucky high school football team in state history. The team went 15-0 and won the Class AAA state championship, destroying Louisville Waggener 56-7 in the title game. In the first week of the regular season, HHS defeated eventual 1998 Class AAAA champion Louisville Male 51-41 in the St. Luke Hospitals Champions Bowl. Led by Mr. Kentucky Football winner Jared Lorenzen and Mr. Football runner-up Derek Smith (both Division I-A recruits), the 'Birds set numerous state records, including most points in a season (801), most points in a championship game (56), largest state championship margin of victory (49), highest per-game yardage average (492.5), most extra points in a season (92), most extra points by a player in a season (Brennan Jones - 90), most touchdowns by a team in a season (113), most total offensive yardage by a team in a game (636), and highest point average per game by a team in a season (53). In addition, Highlands kicker Brennan Jones set a national record for most extra points by a player in a season, with 90. Highlands was ranked 19th in the USA Today Super 25 final 1998 high school football rankings, 14th in the National Sports News Service Poll, 16th in the Comp USA Overall National Poll and 15th in the Prep Nation National Prep Football Poll. HHS finished 1998 as Class AAA champion, regional champion, district champion, and NKAC champion.
1997
The 1997 season ended in disappointing fashion for the defending state champion Bluebirds, as the team was upset at home, 41-35 (2OT), by Covington Catholic in the state Class AAA regional final playoff game. Covington Catholic went on to win the Class AAA title in 1997. This game was later dubbed the "Mud Bowl" on account of the terrible field conditions during the game. Prior to the loss in the regional final game, HHS was undefeated in the state of Kentucky, losing only to Cincinnati Moeller 21-20 during the regular season. Highlands was the favorite to win Class AAA heading into the playoffs. Highlands player Randy Stegman broke the state record for the most touchdown catches in a game, catching five against Simon Kenton. The team finished with an 11-2 record, was district champion, and NKAC champion.
1996
The Bluebirds finished 1996 15-0, defeating Hopkinsville 21-14 in the Kentucky Class AAA state title game. HHS finished the year ranked 21st nationally in the USA Today Super 25 final 1996 high school football rankings. In the Campbell County game, quarterback Jared Lorenzen and wide receiver Josh Hasson tied a state record for the longest touchdown pass play when they connected for a 99-yard touchdown pass. Led by star running back Justin Frisk (who rushed for 1932 yards and 31 touchdowns in 1996), HHS finished the season as Class AAA champion, regional champion, district champion, and NKAC champion.
1995
Highlands advanced to the Kentucky Class AAA state championship game in 1995, but was defeated by unbeaten Bowling Green 28-12 in the title game. The highlight of the season for the 'Birds was dominating Leslie County (quarterbacked by Mr. Kentucky Football and eventual NFL starter Tim Couch) by a score of 47-12 in the Class AAA state semifinal game, held at Highlands. HHS had earlier lost to Leslie County by a score of 44-42 in the Thoroughbred Bowl (the first game of the regular season). Highlands finished 1995 with a record of 11-4 (the other two losses coming to Covington Holmes and Ryle), Class AAA runner-up, and regional champion.
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