Three little sisters fueling Windsor basketball’s quest to repeat


Valley News Staff Writer

Published: 01-12-2023 8:11 AM

WINDSOR — Reese and Sydney Perry’s one-on-one driveway basketball games were intense, physical affairs.

“We had a rule: That we played until one of us started bleeding or crying,” said Sydney Perry, the younger sister and a junior forward on the Windsor High girls basketball team. “Most of the time, it was bleeding. We were definitely pretty intense, which formed us into the way we play now.”

The Yellowjackets’ quest to repeat as VPA Division III state champions this winter will hinge largely on Perry and sophomore guards Audrey Rupp and Sophia Rockwood — both of whom also had an older sister star for Windsor.

The Perry sisters helped the Yellowjackets win a crown last season, with Reese averaging a team-high 15.7 points per game as a senior and Sydney serving as her backup in the post.

Reese is now playing at St. Michael’s College in Colchester, Vt., and Sydney has taken over her sister’s starting role and handled it with aplomb. She leads Windsor with 16.3 points per game, has topped 20 in her last two outings and has also recorded eight double-doubles through 10 games.

Usually the tallest player on the floor against D-III competition, Perry can rapidly accumulate rebounds and blocks. But like her older sister, she can break out some nifty moves in the post, outmaneuvering defenders for easy layups.

“It was a little bit nerve-wracking coming into the season, because I knew I was going to have to fill her shoes,” Perry said. “My feet are bigger than hers, so having to take over her responsibilities, it was scary, (but) I feel like I’ve taken it over well.”

Elliot Rupp averaged 13 points per game for last year’s titlists, and last spring she helped lead Hartford High to its first-ever girls lacrosse state championship.

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But soccer was the sport that took her to the next level. The elder Rupp recently completed her freshman season of Division III college soccer at Moravian University in Bethlehem, Pa., where her highlight was a late goal in a 1-0 win over Lancaster Bible College on Oct. 19.

Like the Perrys, the Rupp sisters frequently went head-to-head at home growing up, which Audrey said helped accelerate her improvement. She saw limited minutes alongside Elliot last season but has grown immensely this year as an outside shooter, ball handler and defender.

“Sometimes there were a lot of fights, but it definitely made me better,” Rupp said. “I don’t know if there was one time where I won. It was exciting to think that I was going to come up and be able to play and compete against other people like her.”

Olivia Rockwood is among the most accomplished basketball players to ever come out of Windsor — the 2020 graduate put up 20-plus points a game in each of her final three seasons, leading the Jacks to a state title as a sophomore with at least 25 points in all four playoff games. Now a junior playing Division I college hoops at the University of Maine, she got off to a hot start this season with the Black Bears, making five 3-pointers in each of her first two games.

Sophia Rockwood never shared the court in high school with her older sister, but she said watching Olivia play at such a high level inspires her to work on her own game. She came off the bench for Windsor last year but has become the Yellowjackets’ best deep threat this winter, sitting on a streak of nine straight games with double-digit scoring.

Together, the three little sisters account for just under 73% of Windsor’s points this season. Kabray Rockwood, father of Sophia and Olivia, is in his third season as the Yellowjackets’ head coach, with Randy Rupp, Audrey and Elliot’s father, as his assistant and head junior varsity coach.

“All these kids got their opportunities a little sooner in life than the older siblings did,” Kabray Rockwood said. “It’s nice to have the kids coming behind them wanting to do the same thing.”

All three fill similar roles on the floor to those of their older sisters did. Sydney Perry has followed in Reese’s footsteps in the post, and Rupp and Rockwood are able to run the point and create shots for themselves and their teammates. All are also hoping to follow their sisters into college athletics, with Audrey Rupp, like Elliot, leaning toward soccer and Perry and Rockwood more clearly focused on basketball.

In the mean time, they have two more chances together to win more championships for both Windsor and their families.

“I don’t think there’s pressure. I think there’s an expectation,” Kabray Rockwood said. “All three of them getting a championship last year, two of them with their older sister, the pressure of getting one kind of goes off. They approach it the right way and don’t let that stuff get to them, and it’s a testament to who they are as people and players.”

Benjamin Rosenberg can be reached at or 603-727-3302.