Anna Woosley begins her second season at Springfield College as a graduate assistant coach with the women's tennis team during the 2019-20 season. Currently working on a Masters degree in Sport Management, Woosley graduated from UMass Amherst in 2017 with a degree in Communications.
During her time at UMass, Woosley led the Minutewomen to their first A-10 Conference Championship and NCAA Division I Championship Tournament appearance in 16 years. An A-10 First Team All-Conference selection, Woosley ranks on all-time singles career wins list at UMass. After graduation, she coached in a high-performance junior tennis academy in Boston.