Jeff Matteo's tenure at Jay from 1995 to 1997 was marked by remarkable achievements. He secured All-State honors for both his Junior and Senior years and reached the pinnacle by earning All-American recognition in his final year. Jeff's soccer prowess extended beyond high school, as he notably participated in the New York State ODP program for seven years. With his club team, the East Fishkill Strikers, Jeff clinched an impressive three ENYYSA State Cup Titles.

His talent transcended college soccer as a four-year starter at St. John's University, where he led the team as captain during his Junior and Senior years. Notably, Jeff's leadership guided the Red Storm to the NCAA Final Four in his Senior year. His professional journey commenced when he was drafted by the Columbus Crew in Major League Soccer, cementing his place among the elite in the sport.

Eric Zegle's legacy at Jay spans from 1997 to 2000, marked by an impressive array of achievements. His outstanding performance garnered All-State and All-American Honors during his Senior year. Notably, Eric secured the school's single-season scoring record with a remarkable 42 goals in the Fall of 2000. Leading the 2000 team as captain, he steered them to claim Jay's sole Class A State Title. Eric's prowess was further highlighted as the MVP of the State Final Four and as the distinguished New York State Player of the Year in 2000.