He played for Colgate University from 2007 to 2011, scoring 54 goals and 56 assists in 149 games. The New York Islanders chose him 171st overall in the 2006 NHL Entry Draft. Day signed an amateur try out contract with the Islanders' farm team, the Bridgeport Sound Tigers, in the spring of 2011 after finishing his career with Colgate. Despite scoring 2 goals and 3 assists in 10 games with the American Hockey League team, Day was not offered a contract by the Islanders and became a free agent.