Cypress Woods volleyball coach earns 500th career win

December 2, 2019

Cypress Woods High School Head Volleyball Coach Ashley Caballero (second from right) poses with her coaching staff after earning her 500th career win as a head coach on Oct. 15 in a Wildcats’ victory over Cypress Park High School. Caballero was part of the inaugural staff at Cypress Woods and recently completed her 19th year as a head coach.
Cypress Woods High School Head Volleyball Coach Ashley Caballero (second from right) poses with her coaching staff after earning her 500th career win as a head coach on Oct. 15 in a Wildcats’ victory over Cypress Park High School. Caballero was part of the inaugural staff at Cypress Woods and recently completed her 19th year as a head coach.

By Ryan Zach, Cypress Woods High School

Dec. 2, 2019—In reaching her 500th career victory as the head volleyball coach at Cypress Woods High School, Ashley Caballero remains just as humbled and grateful as she felt when she and the Wildcats reached other milestones along the journey. The numbers, even simply getting to triple digits, are all reasons to celebrate.

“It seemed absolutely impossible,” said Caballero, who earned her 500th career win as a head coach Oct. 15 in Cypress Woods’ victory over Cypress Park High School. “One hundred [wins] was like, ‘Wow!’ So 500 wins – I just would have never even imagined.”

The Wildcats celebrated the accomplishment following the win and continued the celebration three days later. In addition to congratulatory signs, Caballero was gifted flowers and cupcakes.

Caballero’s coaching career actually began back during her playing days at Henderson State University. She played under current Cy-Fair High School Head Volleyball Coach Donna Benotti.

It took an injury for coaching to go from a thought to an act.

“I got hurt my second year of college, and so I went into coaching,” Caballero said. “I fell in love with it, changed my major and have been coaching ever since.”

When Benotti was named the head coach at Texas A&M University-Kingsville, she asked Caballero to join her as an assistant. Later, she took a chance to lead her own program – Caballero accepted the head coaching job at North Crowley High School in Fort Worth and spent five years with the team.

Cypress Woods High School volleyball coaches and players surround Head Coach Ashley Caballero (center) after she earned her 500th career win as a head coach on Oct. 15.
Cypress Woods High School volleyball coaches and players surround Head Coach Ashley Caballero (center) after she earned her 500th career win as a head coach on Oct. 15.

In 2006, Caballero became part of the inaugural staff at Cypress Woods. She just completed her 14th year with the Wildcats and 19th year as a head coach.

“I’ve been fortunate enough to have a lot of phenomenal kids and teams here, especially when [the school] opened,” she said. “The kids are a part of every one of those wins.”

On reaching the 500-win milestone, Caballero is grateful in knowing she reached a mark many never do in the profession.

“It’s remarkable to even think about having been in the business that long and still be enjoying it,” she said. “The average coach for the female side, stays in it for four years and that’s it. I’ve been able to persevere a little bit to get to that 500. Some people never get to it.”

Caballero admits to being more calm now than in her earlier years as a head coach, and she tries to have more fun. Being the only head coach in program history has also allowed her to establish traditions and core values for the Wildcats.

One such is Cypress Woods will always come together and form a huddle after a game, no matter the result.

“We win together and we lose together, but whatever we do, we’re going to do it together,” Caballero said. “It’s the little things like that that are important.”

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