High School: Guadagnolo played at Jordan-Elbridge High School. He graduated in 2003 before attending the United States Military Academy Prep School from 2003-2004. The Jordan, New York native was an All-American in his senior year of high school while also serving as a team captain. Guadagnolo was selected first-team all-league in 2002 and 2003 and a second-team selection in 2001. He was named All-Central New York in 2003 and played for the Central Empire State Team in 2002. He was inducted into the Jordan-Elbridge Hall Of Fame in 2020.

College-Syracuse University: Started all four years at close defense. A 2008 NCAADivision I National Champion, Guadagnolo served as a team captain for that campaign. He appeared in 57 games during his Orange career, earning USILA All-America honorable mention plaudits in his senior season. That same year, Guadagnolo anchored a defense that finished with a 7.62 goals against average, the lowest mark for a Syracuse squad since 1970.

Over the course of his career for his hometown team, Guadagnolo accounted for 109 ground balls, increasing his total year over year to a high-water mark of 36 as a senior in 2008. During his time with the Orange, Guadagnolo backed the team to a national championship in 2008, besting longtime rival Johns Hopkins 13-10 in the title game. The Orange dropped just two games that season, both one-goal setbacks.

While playing at Syracuse, Guadagnolo had the chance to play with his younger brother, Thomas, during the 2008 season. The Guadagnolos shared in the team’s national championship that season in front of an NCAA outdoor championship record of 48,970 spectators.

Guadagnolo was a member of the Athletic Director’s Honor Roll during his time at Syracuse.

Professional-MLL: Drafted by the Rochester Rattlers in the 2008 MLL draft. MLL Champion in 2008. Played two seasons for the Chicago Machine (2009, 2010).

Personal: Kyle Thomas Guadagnolo. Son of Tom and Gayle Guadagnolo. Three younger brothers. Brother Thomas played for Syracuse University from 2008 to 2011. Kyle and his wife, Brittany (Syracuse Field Hockey Alum), currently reside in Owasco with their three children. Kyle coaches his son’s travel lacrosse team.