Crosby is originally from Andover, MA where he played 4 years at Andover High School as a goalie. During high school, he earned honors of Merrimack Valley All-Conference, Eagle Tribune All-Star, and Eastern Mass Senior All-Star, prior to graduating in 2011. Crosby went on to play for Division II Southern New Hampshire University in Manchester, NH. During his time at SNHU, he began as a goalie and moved to midfield midway through his sophomore season. As a sophomore, he made 9 starts at goalie totaling 87 saves, and 3 starts at midfield grabbing 4 assists. His junior year was spent at midfield, starting all 15 games and tallying 7 goals and 7 assists. He switched back to goalie as a senior, starting all 13 games. Totaling up a 4-year span at SNHU with over 250 saves, 7 goals, and 11 assists before graduating in 2015. Post-graduation he continued a coaching role that began during college with 4Leaf Lacrosse New England based out of New Hampshire. He worked primarily with the middle-school groups at the time, but has since moved to Acton and is starting his third year with the Littlenecks/Clams program.