Born and raised Saint Croix, McGuiness moved with his brothers to West Windsor, New Jersey in 2015[1] and attended West Windsor-Plainsboro High School South, where he played prep soccer.
[3] McGuinness played one year of college soccer for the Cougars of Kean University.
[6] Ramesses was part of the USVI under-20 squad that competed at the 2018 CONCACAF U-20 Championship held in the United States.
[7] Ramesses made his senior international debut on October 12, 2019, in a 2019–20 CONCACAF Nations League qualifying match against Barbados.
On 19 November 2019 he scored his first senior goal for USVI against Saint Martin in the 2019–20 CONCACAF Nations League C.[8]