Addy Sipkin is one of the most gifted guards we have on the Prep Girls Hoops NY rankings. She’s got the ability to light it up from deep, whether it’s getting it off the catch or creating her own shots off the bounce. Addy is a multi-dimensional scorer who can also get to the rim with her tight handle and has a variety of finishes. Sipkin plays with creativity and pace, which mix for a fun watch when she’s on the floor. Her size at the guard position is something that coaches will love as she continues to develop.

Sipkin is pure hooper. Has really burst onto the scene this summer and loves to play. Sipkin is the complete package, a five-tool player coming into her own as her confidence grows in every situation. She has range/accuracy from the perimeter, elite mechanics, but can just as easily rip and go, slicing her way to the basket, and finishing with an array of moves (love her floater). She loves to run the break, can change direction on a dime, and set up teammates with her elite court vision. But make no mistake, Sipkin can close, and she does it with precision and accuracy. She’s a gamer.

Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY (2029) | PG | SHG

Sipkin, a recent champion is exactly what most coaches what salivate over. This is a young leader with a great understanding of the game, someone who willingly sacrifices for the betterment of the team, consistently does her job and works tirelessly to achieve what she’s set out to. It’s hard to imagine a freshman that boosted their stock more this season.

Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY (2029) | CG | SHG

Sipkin is becoming a regular here. She’s mentioned yet again, but this time for her winning traits, tough mentality and poise shown even in the midst of adversity. The sheer impact she has is invaluable, especially considering she’s just a freshman. Coaches have the upmost faith in her for a reason; Sipkin isn’t prone to turnovers, rebounds with the best of guards and can get in going in the scoring department if called upon too. It’s time for Addy to start getting the respect she deserves. This is a ’29 name to remember.

Addy Sipkin (2029) | 5’9 PG | SHG

Addy’s strengths have come to light this season and she’s looking to capitalize on the momentum moving into spring. Sipkin proved to be one of the youngest functional lead guards in all of NEPSAC. It’s not about the flash with her; Addy earned her starting role from building trust from coaches/teammates and coming in each day understanding how to execute at a high level. It’ll be intriguing to watch her in the coming months. This is a player thats going to be on alot of radars very shortly.

Addy Sipkin (2029) | 5’9 CG | SHG

This freshman guard plays with a tough grit and is persistent in her 2-way efforts. Addy isn’t the flashiest of guards, but her strong instincts make her effective. Sipkin possesses a ton of poise no matter the situation, hustles hard on the defensive end plus she can provide a boost in scoring as she takes advantage of favorable matchups when the team calls her number. The balanced guard is in for a big year in 2026; Addy is a no brainer to add to the watchlist.

Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY (2029) | 5’9 CG | SHG

The fabulous freshman Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY is a name that’s going to make statement in 2026. At the Nickerson Showcase, Sacred Heart Greenwich suffered a couple injuries featuring key contributors and guess who stepped up? It was Addy who came through for her squad making a significant effort by racking up multiple steals, rebounds plus some timely assists. Sipkin also added 14 crucial points that helped lift the team up and secure them a victory over Choate. Looking back on a moment like this proves just how instrumental the ’29 guard can be. Look out for much more coverage on Addy; she’s in store for a big year.

Addy delivered an efficient performance with 18 points and 6 rebounds in a dominant win over Greenwich Country Day School, making the most of every possession. She shoots the ball well from deep, knocking down multiple three-pointers, including back-to-back makes early in the second quarter. Her ability to score efficiently while contributing on the glass makes her a steady and reliable offensive option.

Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY (2029) | CG | SHG

A guard that has the capacity to pose a serious threat to opposing teams. She converts on ambitious plays and competes at a high level. It wouldn’t be surprising if Sipkin becomes a staple name within the class at some point.

Addy Sipkin Addy Sipkin 5'10" | CG/PG Sacred Heart Greenwich | 2029 State NY (2029) | CG | SHG

Sipkin is someone who should be on radars as a newcomer to NEPSAC. Addy isn’t the most athletic, but she makes up for in the IQ department. She understands angles and is an efficient shooter, no matter the scenario. Addy will be an intriguing watch over the course of the year.