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Family feud: How the Masoncup family’s tennis success has resulted in a rivalry

Tennis is in the Masoncup family’s blood. Two of the Masoncup boys, Tyler and Aaron (a senior and a sophomore, respectively) made it to the state tennis tournament last year for Geneva.

For their father, Sean, who also found success playing tennis at Geneva, it was a moment that serves as one of his favorite memories as a father.

“My kids, for the rest of their lives, will be able to say, ‘Hey, we qualified together as brothers for the state tournament.’ That was a pretty cool moment that I don’t think I’ll ever forget,” Sean said.

But in Sean Masoncup’s other role, as boys tennis coach at St. Charles North, the moment was also bittersweet. Because they play in the same sectional, every state qualifier from Geneva takes a slot that could have gone to a player from St. Charles North. This means that every time the two schools clash, especially at sectionals, Masoncup is torn between his role as coach and his role as father.

  St. Charles North tennis coach Sean Masoncup, far left, with his sons Tyler, center right, and Aaron, center left, who play for Geneva High School and are coached by their grandfather Hal, far right, Thursday, April 10, 2025 at Geneva High School. Brian Hill/bhill@dailyherald.com

“It’s probably one of the hardest things I’ve done in coaching. They’re my blood, they come first, but … if we see them in a sectional or in (the DuKane Conference), they’re somebody my team needs to beat,” Sean said.

To add to the family rivalry dynamics, Sean’s father, Hal, is also deeply invested in Geneva tennis. Hal was one of Sean’s assistants at St. Charles North until Tyler, the older of his grandsons, enrolled at Geneva. After that, Hal — who also played Division I tennis — took on a volunteer assistant role to help bolster his grandson. For Tyler Masoncup, having his grandfather in his corner has been the ideal situation for his game.

“Whenever I have a question about anything when it comes to tennis, I go and ask him, because he’s been coaching for 40 years,” Tyler said of his grandfather. “He’s probably the best coach I’ve ever had.”

  St. Charles North tennis coach Sean Masoncup, far left, with his sons Tyler, center right, and Aaron, center left, who play for Geneva High School and are coached by their grandfather Hal, far right, Thursday, April 10, 2025 at Geneva High School. Brian Hill/bhill@dailyherald.com

And that coaching skill is embedded in the family’s legacy. The Masoncup family has spent two generations coaching tennis at a high level, and that streak is unlikely to end anytime soon. According to Sean, Aaron is almost definitely going to be the next head coach in the Masoncup lineage.

“Aaron for sure … will be, that’s what he wants to do,” Sean said. “I’m fairly certain that there’ll be another Masoncup in the area at some point, coaching and teaching. Who knows? Maybe he’ll come back and coach with me.”

But for now, Aaron is focused on playing. He hopes to make a second consecutive trip to the state tournament with his brother, which would mark Tyler’s third straight appearance. But with this season being the last for Tyler in high school, Aaron wants to make sure their stay in the postseason this year is a little longer than last year’s.

“I want to try as hard as possible to get Ty his one win at state before he goes off to college,” Aaron said. “That’s pretty much it. I just want to get Ty his one win.”

Three generations of the Masoncup family have been driven by a love for tennis, passed from one generation to the next. And for the Masoncups, getting the chance to participate in the sport they love, even if it does mean competing against each other, is always worth it. As Aaron put it, “It’s just a fun experience all around.”

  St. Charles North tennis coach Sean Masoncup, middle, with his son Tyler who play for Geneva High School and are coached by their grandfather Hal, left, Thursday, April 10, 2025 at Geneva High School. Brian Hill/bhill@dailyherald.com
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