Head Coach Leon Calleja’s Relaxed Yet Competitive Nature Has Guided Boys Tennis To Undefeated Streak

Being undefeated so far in the season and the top contender of the Class A Division, Head Coach Leon Calleja is the foundation of the Boys Tennis program’s success. Reflecting on his experiences, Calleja leads with care and humility.

Having played tennis at the young age of eight years, Calleja was naturally gifted in the sport and was ranked in the top 100 in the state of Florida, despite never having formal training. However, Calleja did not continue pursuing tennis at Amherst College.

Calleja said, “I played for my public district team, which was a lot bigger, which was fun. I was always the smallest player on the team, which was good and bad, but I enjoyed it. [I] love to play, even though I was the smallest player, I loved to serve and volley.”

Highlighting Andover’s curriculum, Calleja recalled his own experiences in grappling with a rigorous academic program while playing tennis. Understanding the challenges of the environment, Calleja reiterated the importance of leading the team with confidence and resilience.

“Tennis is a really mental game… Know[ing] that if I had a chance to train for six hours a day, just wondering how good a player I might become… Those are some of the things that I think Andover tennis players particularly sort of wrestle with because the Andover academic experience is definitely one that doesn’t allow you to sort of train for six hours a day, and really, cultivate your mind as much as your playing ability,” said Calleja.

By allowing players to have the freedom to tailor their practices, Calleja allows the team to collaborate and lead. Chase Burke ’25 commented on the method, noting its importance for bringing in the team’s ranging tennis capabilities.

“By leading our own practices, everyone knows their weaknesses [and] their strengths.
And we’re good at compromising if some person needs to work on something, another person needs to work on something else… I believe it makes us more independent. Like a lot of times coaches kind of think they know more than they actually do. And it can lead to players not wanting to practice… But I think having this freedom leaves everyone in a super positive mindset and keeps everyone working super hard,” said Burke.

Ben Shin ’26 shared similar sentiments, noting how Calleja’s relaxed yet competitive spirit eases pressure during matches. Calleja strikes a balance between providing feedback and room for players to overcome challenges.

Shin said, “He wants us to be really competitive, but also relaxed. And just be happy. I mean, just have fun out there. That’s all it is. Tennis is really easy if it’s fun… We run practice ourselves in the drills, but he’s always there to give us technical tips and stuff. I think it just allows us to be more independent and relaxed on the court. He’s not like adding pressure onto us every single time we play.”

Burke emphasized Calleja’s experience in leading the team to numerous New England Preparatory School Athletic Council victories.

“He knows the work that we have to put in. And, he’s going to keep us on top of our game if we’re slacking off in practice or we don’t want to be there. He’s going to make an environment that makes you want to be there and keep going, keep pushing us to our limits,” said Burke.

With the team’s undefeated season, Calleja hopes to continue the streak against challenging competitors this week. Soon facing the long-time rivals, Phillips Exeter Academy (Exeter) and Roxbury Latin, Calleja looks forward to the team’s trajectory.

Calleja said, “We’re maintaining our humility in the face of beating some really challenging teams. We have Roxbury Latin coming up on Friday. We have Exeter coming up on Wednesday. Exeter is going to be a really tough team… Roxbury Latin, we haven’t beaten them in a few years, I think that will be a good test for us to see about all the undefeated teams on Friday.”