25 January 2013, Winchester agreed to join FF Jaro of the Veikkausliiga on a one-year loan following a successful two-week trial. One week later, he scored a seventh-minute goal in his debut for Jaro during a league cup match against VPS. On 20 February, he provided his second goal in three league cup matches with a penalty kick in a win over RoPS. However, after making seven consecutive appearances in the league cup, Winchester underwent surgery on 13 March for an injury to his Achilles tendon. On 5 May 2013, Winchester made his league debut for FF Jaro against HJK after coming on for Markus Kronholm in the 62nd minute. After five consecutive league appearances, including three as a substitute, Winchester scored his first league goal in a 2–1 win over FC Lahti on 23 May. He scored two more goals in the next three league matches against TPS on 26 May and a week later against RoPS. Winchester later scored in consecutive matches against MYPA and FC Honka on 27 and 30 June. On 27 July, he recorded a brace in front of Jakobstad's second largest crowd for a football match in a 2–1 derby win over VPS. However, a string of illnesses and injuries kept him sidelined for Jaro's final six matches. Prior to his return to Trinidad and Tobago in October 2013, Winchester agreed to a one-year contract extension with Jaro through the end of the 2014 Veikkausliiga season. In his first season in Finland, Winchester recorded eight goals in the Veikkausliiga and ten goals in all competitions. Following his loan to FF Jaro, Winchester returned to parent club, W Connection, for three months before his second loan to the Finnish club. In his short return with the Savonetta Boys, Winchester appeared in nine Pro League matches and scored five goals. On 21 January 2014, he scored a double over rivals San Juan Jabloteh, which was followed four days later with another goal against North East Stars. Before again departing for Finland, Winchester scored a further brace on 8 March against St. Ann's Rangers to extend W Connection's league lead to eight points en route to the club winning its fifth Pro League title. On 19 March 2014, Winchester rejoined FF Jaro on another one-year loan for the 2014 Veikkausliiga season. Two weeks later, he made his return league debut for the club having started as a