Ryan was a standout center fielder for the Holy Cross softball team in the early to mid 2000s. A first team All-Patriot League selection during each of her final three seasons, she holds the school records for career hits (179) and career at-bats (559), while standing third all-time in career runs scored (84), fifth in career batting average (.320) and career stolen bases (40) and ninth in career slugging percentage (.402). Ryan’s top season came as a senior in 2005, when she hit .384 with 12 doubles, 31 runs scored and 10 stolen bases.
Also an outstanding student, Ryan was chosen as a third team Academic All-American in 2005, while earning Academic All-District honors two times. She was also named the 2005 Crusader of the Year, and was selected as Holy Cross Valedictorian for the Class of 2005.