O. Sinclair

Orlando Sinclair joined Deportivo Saprissa's academy at the age of ten and made his first-team debut on 4 October 2018, scoring in that match. He spent much of the following two seasons away from the club on loan, first with CS Uruguay de Coronado in Costa Rica's Segunda División, then with Loudoun United FC in the United States, where he made 24 appearances and scored three goals for D.C. United's affiliate side before returning to Saprissa in December 2019. A further loan followed in 2020 with New England Revolution II, where he added two goals in 14 outings.

Sinclair returned to Saprissa permanently in January 2021 and signed a contract extension later that year running through 2024, since renewed to the end of 2026. He was part of the Saprissa squad that won the Liga FPD Clausura 2021 title.

His full international career began on 21 August 2021, when he came on as a substitute in the 63rd minute of a friendly against El Salvador that finished goalless. He has yet to score for Costa Rica.

At club level Sinclair plays with the number 24 on his back, though he wears 19 for the national team.