Chip Boling: Teaching Life Lessons Through Tennis

For more than two decades, Chip Boling has been a fixture on the courts at Howard High School, serving as a coach, mentor, and believer in what tennis can do beyond the court. His unwavering commitment, quiet leadership, and a deep belief that the court is more than a place to win matches, but also a classroom where character is built, confidence grows, and lifelong love for the game takes root. He will be receiving the Tennis in the Classroom Award at the Tennis Creates Gala on Dec. 6. 

A Legacy of Coaching and Connection

Chip’s coaching career spans 20 years at Howard High School, where his influence extends far beyond the scoreboard. His teams have earned over 350 career wins, four regional championships in the last five years, and numerous top finishes in the Howard County Cup. Yet for Chip, those numbers tell only part of the story.

“What keeps me going is the kids I work with,” he shared. “Watching them grow as tennis players fuels me to keep coming back.”

This year, his girls’ team, with half of the roster brand-new to tennis, finished second in the county. It’s the kind of achievement that perfectly captures Chip’s approach: patience, player development, unshakable belief, and constant encouragement. He recalls one player who struggled as a freshman but returned her sophomore year transformed.

“She said, ‘Your expectations were so high, and you really care about how we can improve. I just wanted to make you proud.’ That’s what it’s all about.”

Building Bridges for the Sport

Beyond his team, Chip’s dedication has rippled across Maryland. Representing Howard and Anne Arundel counties for Maryland Public Schools, he’s been a driving force in modernizing high school tennis.

After attending a training at the USTA National Campus, he spearheaded the rollout of USTA Serve Tennis across Howard County, registering every player, running tournaments through the system, and setting a new benchmark for accessibility and transparency.

“I said to myself, ‘We need to do this. I can make it work,’” Chip explained. “It allows us as coaches to see how players are doing, gives players data to improve, and makes sure competition stays fair.”

He’s now working to expand the platform statewide, ensuring every public school program in Maryland benefits from this more connected, player-focused system.

Serving the Game, Not Himself

For over 20 years, Chip has served as a USTA tournament director, running events at Howard High School and Forest Hill Swim and Tennis Club. From Orange Ball to L4 tournaments, he’s there making sure players not only compete but also learn.

“Being a tournament director isn’t just about competitive play,” he said. “It’s about teaching kids the proper rules and helping them understand the game.”

His reputation is one of fairness, care, and generosity. Chip often offers full refunds when issues arise, rewarding players, and ensuring each event feels meaningful. Parents and players often wonder why he doesn’t run more tournaments. His answer is simple: quality over quantity.

“To Chip, it’s not about the money,” one colleague said. “It’s about growing the sport.”

Family, Faith, and Fuel for the Future

Balancing his many roles hasn’t always been easy. As a coach, tournament director, and Director of Racket Sports at Forest Hill Swim and Tennis Club, Chip spends countless hours on the court. What keeps him going is not only his passion for tennis, but also his wife and two children.

“It’s hard to be a coach when you have a young family,” he admitted. “But my wife and kids always ask how my teams have done. My kids love coming to practice and helping run camps. I’m grateful to all three of them.”

At Forest Hill, Chip oversees all racquet programs, including pickleball, but his heart always returns to youth tennis. He believes every child can be a future ambassador of the game, carrying forward the values of respect, resilience, and sportsmanship.

Why Chip Boling Inspires Us

When Chip first learned he had won the Tennis in the Classroom Award, the honor came with a moment that perfectly sums up his humble spirit.

“My daughter saw the paper and said, ‘It’s about time someone recognizes you for all you do!’” Chip laughed. “But really, I think it’s an accomplishment for all the players who have played for me. Their hard work makes me look good.”

For Chip, coaching isn’t about personal glory, but it’s impact on young student-athletes. He hopes his story encourages others to step up for their communities, whether as coaches, volunteers, or officials.

“We need more people who care about the sport,” he said. “Coaching can’t be about yourself. It’s about the players. We are molding them into women and men of the future.”

And that’s what makes Chip Boling more than just a coach. He’s a teacher of life lessons, a builder of character, and a reminder that tennis creates something far greater than champions. 

Join Chip and the Tennis Creates Awards honorees at the Tennis Creates Gala on Dec. 6 at the Salamander Hotel in Washington DC. All proceeds from the Gala and Fantasy Clinic benefit USTA Mid-Atlantic Foundation’s mission to champion tennis for healthier lives and communities, making the sport accessible to all in the Mid-Atlantic.  Through programs like Girls Rule the Court™, Jr. Player Scholarships, Facility Restoration Grants, and Community Engagement Grants, the Foundation is ensuring that every person, regardless of background or zip code, can experience the lifelong benefits of tennis.

For more information, Tennis Creates Gala and Fantasy Clinic tickets, and sponsorship opportunities, please visit TennisCreatesGala.com. 

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USTA Mid-Atlantic Foundation is a 501(c)(3) nonprofit organization committed to promoting tennis and its physical, social, and emotional health benefits. Learn about our impact in the region and how USTA Mid-Atlantic creates community, character, and well-being.