Winston made his debut in the Costa Rican Primera División in 1999 with only in 17-year-old, playing with his hometown team Limonense and scored his first goal back on 28 November of the same year, he played this season mostly as a substitute, because he was competing at that moment against some players that succeeded during the next few years, like Kurt Bernard, Andy Herron, Rayner Robinson and Ricardo Douglas for a place in the starting line-up. The following season and after the sale of most of the players mentioned before, it was usual to see him in the starting line-up making a dangerous offensive triplet with Victor Núñez and Andy Herron.