Foregoing a college soccer career, Sylvestre signed for the Vancouver Whitecaps Residency program in February 2010.
Sylvestre was part of the IMG Soccer Academy in Florida, before moving to the Vancouver Whitecaps FC Residency in 2009.
[13] On January 14, 2019, Sylvestre became the first goalkeeper signed by USL League One expansion team Forward Madison FC.
[14] Sylvestre was transferred to USL Championship team Miami FC on January 23, 2020, for an undisclosed fee.
[19] In January 2023, Sylvestre joined the technical staff of Savannah Clovers FC ahead of their inaugural season in the National Independent Soccer Association.