The Waterbury Times|TWT Sports Desk|Published Mar 13, 2026

Correction- 4th- 2012 advanced to Final Four losing by 1 to Career Magnet.

Waterbury- The Wildcats are chasing history again.

After advancing through the early rounds of the state tournament, Wilby High School now heads on the road tonight to face Sport and Medical Sciences Academy (SMSA) in the quarterfinals. A win would send Wilby to the Final Four, marking just the third time in the last 30 years the program has reached that stage.

For longtime Waterbury basketball fans, the moment brings back memories of two other playoff runs that energized the community.

Waterbury High School Sports News

The 2005–06 Run

The 2005–06 Wildcats, who finished 19–7, battled through the tournament with key wins over:

• Suffield High School – 59–39
• Sacred Heart High School – 61–44
• East Lyme High School – 48–43

The run ended in the semifinals with a hard-fought 58–53 loss to Berlin High School, but that team remains one of the most memorable in Wilby history.

The 1998–99 Tournament Run

From the Archives: 1999 Wildcats

One of Wilby’s most memorable tournament runs came during the 1998–99 season, when the Wildcats finished 12–8 but caught fire in the state tournament.

That team defeated Tolland High School in overtime on the road before adding wins against North Stonington High School and Cheney Technical High School.

The run eventually ended against Kolbe Cathedral High School, but the roster featured standout forward Ryan Gomes, who would go on to star at Providence Friars men’s basketball and later in the NBA.

Former Player Perspective:

Former Wilby player and current Tyrell Middle Coach Wes Heyward, who was part of the 1998–99 playoff run, shared his reflections on that historic season:

“I was just a bench player, but it felt like everyone—even the role players—knew how serious this was. The practices leading up to the game felt different. The layup lines felt different. The energy inside the gym was different. Being one of the last two teams in the state tourney, the whole city was behind us. Sucks that we couldn’t get over the hump and beat Kolbe Cathedral! That playoff run meant a lot to the city. Everyone took their role seriously. That was a game where you didn’t have to hype yourself up to play—the energy was palpable.”

This sense of citywide support carries into today, as Wilby’s 2025–26 team looks to join the 1999 and 2006 squads in Final Four history.

Adding to the excitement is the connection with local youth basketball. Tyrell Middle School, located at 500 Todd Rd, Wolcott, CT, is a key hub for community hoops, hosting travel basketball teams, Connecticut Basketball Conference games, and middle school-level competitions. Coaches and players from Tyrell are watching closely, seeing the Wildcats’ journey as inspiration for the next generation.

“Our boys are seeing what it takes to get this far,” said the Tyrell Middle School coach. “It’s about energy, preparation, and understanding your role—exactly what Wilby has done.”

For Waterbury, the Wildcats’ run is more than a game—it’s a community moment, a reminder of how local hoops unite the city, past and present.

A New Chapter for Wilby

Now, the 2025–26 Wildcats have a chance to add their own chapter to that history.

A victory tonight over SMSA would put this group in rare company — joining the 1999 and 2006 teams as the only Wilby squads in three decades to reach the state Final Four.

For Waterbury, the moment is about more than basketball. Tournament runs have long brought the city together — alumni, former players, students, and neighborhood fans all rallying behind the Wildcats.

Tonight, another opportunity awaits.

What You Need to Know About This Year’s Wilby Wildcats Before Tonight’s Quarterfinal at SMSA of Hartford

---

Game: Wilby vs. SMSA
Round: State Quarterfinals
What’s at stake: A trip to the Final Four

If the Wildcats win, the echoes of 1999 and 2006 will grow louder — and a new generation will write its place in Wilby basketball history.

---

CTA:
Were you part of the 1999 or 2006 Wilby playoff runs? Share your memories with the Waterbury Times Sports Desk as the Wildcats chase another Final Four appearance.

Related Waterbury Sports News:

Wilby Wildcats 2025–26 Basketball Preview: A Summer Championship Raises Expectations

Wilby Wildcats Outlast New Fairfield, Advance to Next Round of State Tournament

Crosby Senior Casleem Washington Wraps Up Senior Season, Eyes State Tournament

WCA Survives Crosby in Instant Classic, Advances to 4th Straight NVL Title Game