2009-10: After playing his youth hockey in the Florida Junior Panthers program, Shayne Gostisbehere enrolled at South Kent School in Connecticut as a junior. In 33 games he scored 6 goals with 27 assists. South Kent finished 17-15-1 and lost to Dexter in the quarterfinals of the New England prep school small schools tournament. Gostisbehere committed to playing college hockey at Union College in 2011-12.
2010-11: Gostisbehere skated in 24 games for South Kent School as a senior. He scored 7 goals with 29 assists and had 32 penalty minutes. South Kent entered the small schools tournament as the top-seeded team but was upset by New Hampton, 5-4 in overtime, in the quarterfinals; finishing 21-9-1.
2011-12: Gostisbehere had a memorable freshman season at Union College as the Dutchmen won the ECAC Hockey regular season and playoff championships and reached the Frozen Four for the first time in school history. In 41 games Gostisbehere scored 5 goals with 17 assists and was plus-18 with 20 penalty minutes. He was selected to the ECAC Hockey All-Rookie Team and was invited to USA Hockey's Evaluation Camp for the 2013 World Junior Championship. Ranked 148th amongst North American skaters in Central Scouting's final rankings prior to the 2012 NHL Draft, he was selected by Philadelphia in the third round (78th overall).