Medina finished the 2016 spring season as the NJCAA national runner-up. She was invited to the Oracle Cup as number two seed due to her 2016 success and finish in the Florida ITA Regional Tournament in Melbourne, Florida this fall. Medina responded by winning the junior college bracket and proving her worthiness of the invitation. Included was a convincing victory over regional foe Eastern Florida State College. Maria Medina earned a place in history, becoming the second Manatees tennis player to achieve win this tournament.
The Oracle Cup features a championship tournament which includes the winners of the NCAA Division II, NCAA Division III, NAIA, and Junior College brackets. This event was formerly known as the "Super Bowl". After winning the Junior College bracket, Medina qualified for the Oracle Club Championship. She defeated the NCAA Division III champion in the semi-finals and qualified for the national championship match. In the end, Maria finished as national runner up to the NAIA champion. Again she made SCF Tennis history, as her finish was the highest finish of any player since the inception of the SCF tennis program.