Who is Henderson County High School's biggest rival? It depends on the sport

HENDERSON, Ky. — Who is Henderson County’s biggest rival?

It’s a question that has been posed occasionally through the years. The truth is, Henderson County doesn’t have one true rival as there would have been back in the day when City High and County High locked horns.

Henderson County’s biggest rivals vary from sport to sport.

I decided to investigate those rivalries and determine which is the biggest.

Girls basketball: Cory Coble doesn't expect a complete makeover needed at Union County

Here are the criteria I used:

• Competitiveness: It’s not a rivalry if it’s not competitive. Both schools must have some success. If one team wins most of the time, it’s not much of a rivalry.

• Longevity: Weight is given to a long-running series, especially if the teams play annually.

• Significance: District or region opponents carry more weight because more is riding on the outcome when they regularly have rematches for district or region titles.

• Intensity: A good rivalry is nothing if there’s not a bit of nastiness or drama involved.

4. Volleyball: Caldwell County

Volleyball isn’t one of Henderson County’s high-profile sports, but the Lady Colonels’ rivalry with Caldwell County is as strong as any in the Second Region.

The 11 other volleyball-playing schools in the region know the path to a regional championship goes through Henderson County and Caldwell County.

The schools have combined to win 15 Second Region championships, including 14 of the last 15.

Though Henderson County leads the series 22-12, each team has had stretches of dominance over the other. Caldwell County won seven of eight matches over the Lady Colonels from 2007 through 2010 as the Lady Tigers won three of their six regional championships in that period.

Henderson County won 11 straight matches from Caldwell County from 2012 through 2017 as it began a run of seven region championships in eight years.

The series has been more balanced recently with Henderson County holding a 4-3 edge, but the Lady Colonels have won when it matters most as they won three of the last four region titles.

3. Football: Owensboro

Football is the marquee sport for Henderson County, but football does not have a marquee rivalry.

The closest Colonel football comes to a rivalry is the one with Owensboro.

It’s a tenuous rivalry at best. Other than a period in the early 2000s, the schools have been in different classes so only bragging rights are at stake when they meet.

Owensboro has more intense rivalries with the other schools in its community – Apollo, Daviess County and Owensboro Catholic.

More football: Dusting off the old playbook may have Henderson's offense going in right direction

But the Henderson County-Owensboro rivalry has history on its side. The football series between the communities goes back to 1895 and includes the long-standing Thanksgiving game between Henderson’s city school and Owensboro.

In recent years, the Henderson-Owensboro game has moved to the end of the regular season. While it has no bearing on district or postseason play, the outcome is important to older fans in both communities.

“(The importance of the series) is what this game means to the community,” said Henderson County coach Josh Boston, who has played and coached in the series with Owensboro for most of the past quarter of a century. “They don’t care what you did against Central Hardin or Calloway County. They want to see what happens against Owensboro.”

71 years in the making: Small, resilient Lyon County has a basketball celebration

The Henderson County-Owensboro series began in 1957 and the schools have played every year but five since then.

Owensboro leads the series 37-24 and has more wins over Henderson County than any other school. Only Daviess County has played the Colonels more times (72). From 1993 through 2020 when the game was canceled because of COVID, Henderson County and Owensboro played every season.

While the Red Devils do have bigger rivals, Henderson County is still an important opponent on their schedule.

“Our kids care a lot. Their kids care a lot,” Owensboro coach Jay Fallin said. “Our coaches really want to win. Their coaches really want to win. Our community really wants to win and their community really wants to win. It ends up being heated typically.”

Because Owensboro is a non-district opponent, other games take on greater importance for the Henderson County players. McCracken County took over the preeminent spot on the Colonels’ regular-season schedule with the school opened in 2013.

The Mustangs won the first six games in the series until the Colonels claimed their first win in 2019.

“(The Owensboro game is) not that big of a deal to the players,” Boston said. “If you asked the kids who they’d rather beat, and it would be McCracken.”

McCracken County, like Owensboro, has bigger rivals too – like Paducah Tilghman.

2. Girls basketball: Webster County

Unquestionably the Second Region’s top two programs since girls basketball resumed in 1975, Henderson County and Webster County often go head-to-head as many as four times in a season.

Though Henderson County has a decisive 84-51 lead in the series, no school has more wins over the Lady Colonels than Webster County. It’s not even close. Union County, the other school in the Sixth District, has the second-most wins over Henderson County with 32.

“We’ve been fortunate to come out on top on most of them, but It’s been a battle every time,” said Jeff Haile, who just completed his 36th season as Henderson County's coach.

Tying the programs together is Phil Gibson, who is the architect of the Lady Trojans' success during his 17 seasons as their coach. He has spent the past 14 as an assistant on the Henderson County staff after a 12-year stint as the Henderson County boys coach. Gibson led Webster County to the first two of the school’s five regional titles in 1981 and 1984.

What we learned: Henderson County wins its fourth straight region title

“It has been like this since Coach Gibson was there,” Haile said after the teams played for the Second Region championship last month – the seventh time that has happened since 1998. “These are district games. We’re not very far apart. The kids know each other. The coaches know each other and are friends in fact.”

Of the current Second Region schools, Henderson County has the most region championships with 18. Webster County is second with five and is also second to Henderson County in trips to the region final with 15. Henderson County has played in the title game 24 times.

1. Boys soccer: Madisonville

Since soccer began at Henderson County in 1983, the Colonels have played Madisonville 72 times – more than any other opponent.

Henderson County has a slight lead in the series 38-30-4. Daviess County is the only school with more wins over Henderson County with 32.

While I would stop short of saying there is bad blood between the programs, no series brings the heat like this rivalry. Matches can teeter on the edge of a brawl.

Benson Pryor has participated in the series with Madisonville since the mid-1990s, first as a player and the last 20 as a coach.

“As a player, I remember thinking that it was a big game because they are always good. You might play them two or three times a year,” he said.

The style of play in the early days fed into the intensity of the matches.

“Back when I played, soccer was a more physical sport. Physicality won out a lot of times,” Pryor said. “It’s still physical, but the players are so much more technical than when I played.”

Though the players rely more on finesse today, the rivalry hasn't cooled down much. “I think it’s just as intense,” Pryor said.

Boys soccer: Braeden Myers-Curry scores three goals as Henderson advances to region final

The schools were in the same district until 2012 when the regions were realigned. Henderson County and Madisonville have played 22 times in the postseason including every year from 1998 through 2011.

The Colonels hold a 12-10 edge in the postseason and the schools have played each other in the regional four times with each winning two.

Each school has had short stretches of dominating the other.

“It goes back and forth. There was a stretch when they were considerably better than us. My first few years (as head coach) we were better than them,” Pryor said. “Right now, it’s really competitive. We win by a goal, We tie. They win by a goal. It’s usually like that.”

Adding to the intrigue of the Henderson-Madisonville rivalry is the influence of the Harris Agisilaou coaching tree. Agisilaou coached the Colonels from 1986 through 1996. Future Henderson County coaches Brian Crafton and Pryor played for him.

Agisilaou’s son Christakis just finished his fourth season as Madisonville’s coach. His brother Nikos is an assistant coach for the Maroons.

The schools’ proximity and the familiarity between the players who often play club soccer together brings some heat to the rivalry.

“Players (on both teams) probably circle that game on the calendar as one they want to win,” Pryor said.

This article originally appeared on Henderson Gleaner: Who is Henderson County's biggest sports rival? Depends on the sport