2003
The Highlands Bluebirds finished 2003 as Kentucky Class AAA state runner-up with a 12-3 record. The 'Birds went undefeated in district play and advanced all the way to the state championship game, held at Papa John's Cardinal Stadium in Louisville, Kentucky. There, Highlands was defeated 44-10 by defending state champion Boyle County. Boyle County defeated Highlands twice in 2003, with the regular season game being a one-point loss at Boyle County. Highlands' only other defeat came against Danville, a team which went on to win the Kentucky Class A championship in 2003. HHS finished 2003 as Class AAA state champion runner-up, regional champion, district champion, and NKAC champion.
2002
The 2002 football season ended on a bit of a sour note for the 'Birds, as they were defeated by Rockcastle County in the Class AAA state semifinal game by a score of 45-6. The game was held at Rockcastle County. Highlands finished the season with a 10-4 record, the four losses coming against Lexington Henry Clay, Louisville Male, Dixie Heights (in overtime), and Rockcastle County. The 'Birds did manage to roll through district play undefeated in 2002, relying upon a strong passing game. HHS finished 2002 as regional champion, district champion, and NKAC champion.
2001
A young, inexperienced Highlands team came up short in its bid to win four consecutive state titles in 2001. The Bluebirds began the season with a shocking 0-2 record (the losses coming to Lexington Henry Clay and Louisville Male), but then managed to win their remaining regular season games, including the district games. After winning the first round Class AAA playoff game, the 'Birds hosted arch-rival Covington Catholic in the second round. Although Highlands had easily won the regular season district contest, Covington Catholic pulled off the upset, beating the 'Birds 18-15. Thus, Highlands finished 2001 with a 9-3 record. College Division I-A recruit Rob Smith, a senior offensive lineman, was named Gatorade Kentucky High School Football Player of the Year, USA Today All-American, Parade Magazine All-American, NKAC Player of the Year, "That's My Boy" Award recipient (for the most outstanding scholar-athlete in northern Kentucky football), and was invited to the U.S. Army All-American game. HHS finished 2001 as district champion and NKAC champion.
2000
The 2000 season was a very successful one for the Bluebirds. Highlands captured its third straight Kentucky Class AAA title in a row, defeating Owensboro 48-27 in the championship game. The 'Birds finished 2000 with a 14-1 record, the only loss being a 21-14 defeat by Cincinnati Elder at Paul Brown Stadium in Cincinnati, Ohio. Highlands, led by seniors and Division I-A college recruits Gino Guidugli, Brent Grover, Brett Hamblen, and Ben Scott, was never seriously challenged in the state of Kentucky, racking up 729 points while only surrendering 206 throughout the entire year. The tone for the season was set in the first week, as Highlands beat eventual Class AAAA runner-up Louisville Trinity 42-29 in the Recreation Bowl. Highlands finished the year ranked first in the entire state, regardless of classification, by Dave Cantrall of the Lexington Herald-Leader. Highlands set several state records in 2000, including most passing touchdowns in a season (59), most individual touchdown receptions in a season (Brett Hamblen - 27), most passing touchdowns in a game (9), most individual touchdown receptions in a single game (Brett Hamblen - 6), and most consecutive state titles by a Class AAA team (3). National recognition included being ranked 13th nationally in the USA Today Super 25 final 2000 high school football rankings, 12th in the National High School Football "Tony" Poll (Tony Bianco), 10th in the Dick Butkus National High School Football Poll, and 47th in the Fox Fab 50 Final Poll. Brent Grover, a top player for Highlands, was invited to the U.S. Army All-American game. HHS finished 2000 as Class AAA champion, regional champion, district champion, and NKAC champion.
1999
Highlands maintained the program's winning tradition in 1999, repeating as Class AAA champion. The team went undefeated against Kentucky teams, and only suffered one loss (to Cincinnati Elder, 35-14). The 'Birds easily handled Owensboro 48-10 in the title game to cap off a 14-1 year. HHS was ranked 18th nationally in the final National High School Football "Tony" Poll, 16th nationally in the Dick Butkus National High School Football Poll and 45th nationally in the Fox Fab 50 Final Poll. Star junior Brett Hamblen was named the Northern Kentucky Player of the Year, and Coach Dale Mueller was named Northern Kentucky Coach of the Year. In 1999, Highlands broke the state records for most individual career extra points (Brennan Jones - 170), most points scored in playoff games (295), most points scored in a state semifinal game (76), and HHS tied the state record for the most points scored in a playoff game (76). Highlands' high-powered offense scored 730 points on the season. The team finished 1999 as Class AAA champion, regional champion, district champion, and NKAC champion.
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