The Waterbury Times|Published Dec 30, 2025

WATERBURY, CT — Two of Connecticut’s oldest and most storied high school basketball programs face off this week as 5–0 Hillhouse takes on 2–0 Wilby. This game isn’t just another early-season matchup — it’s a century-long legacy of basketball excellence converging on one court.

Waterbury High School Basketball: Hillhouse Tops Wilby 95–68

A Century of Connecticut Basketball History

Wilby High School

Wilby High School holds a unique place in Connecticut basketball history. In 1923, Wilby became the first school in the state to compete in a state championship game — and claim victory. This milestone set the foundation for organized high school basketball in the Nutmeg State, establishing Wilby as a program that values tradition, fundamentals, and early leadership in the sport.

Wilby Improves to 2–0 with Double-Digit Win Over Kennedy

Hillhouse High School

Just two years later, Hillhouse High School ( New Haven ) would claim the first of what would become 24 state championships. From 1925 onward, Hillhouse developed a dynasty, combining skilled coaching, player development, and a culture that prizes sustained excellence. The program has become synonymous with winning in Connecticut and has produced generations of players who have left lasting marks in collegiate and professional basketball.

Undefeated Teams Meet – 100 Years in the Making

This matchup carries weight beyond the current season. With Hillhouse at 5–0 and Wilby at 2–0, both teams enter the S.A.G. Tournament undefeated. For fans of Connecticut basketball, this is 100 years of history colliding on a single court. The game represents more than a tournament win — it’s a living reminder of the deep roots both programs have planted in the state’s basketball tradition.

Even before the tip-off, the narrative writes itself: the first state championship winner (Wilby) versus the first dynasty (Hillhouse). Coaches, alumni, and historians alike will note the symbolism — a century of basketball excellence distilled into one early-season matchup.

NVL Boys Basketball Power Rankings Update: Early Season Shakeups After Two Weeks of Play

Looking Ahead

No matter the outcome, the matchup between Hillhouse and Wilby is a must-watch for anyone who cares about Connecticut high school basketball history. Both programs have proven that excellence is built over decades, and this game is the latest chapter in that storied rivalry.

For more Waterbury Highschool Sports

Stay link

Waterbury High School Sports News