Early career Born in
Kingston, Jamaica, Flemmings began his career in the youth ranks of
Tivoli Gardens.
Tivoli Gardens In 2013, he made his debut for the first team in the
National Premier League. He was unpaid during the 2013 season with Tivoli Gardens to ensure that he wouldn't ruin his chances of playing collegiate soccer in the United States. During the 2015–2016 season Flemmings led Tivoli Gardens in scoring with eight goals, including a late game winner on 23 November 2015 which helped his club to a 2–1 victory over
Boys' Town FC.
New York Red Bulls II After months of speculation, Flemmings signed with
New York Red Bulls II of the
United Soccer League on 25 March 2016. On 2 April 2016, during his first appearance, Flemmings recorded his first goal and assist with the club in a 2–0 victory against
Louisville City. On 22 May 2016, Flemmings scored a late match winner helping New York to a 1–0 victory against
FC Montreal. On 12 August 2016, Flemmings helped New York to a 5–1 victory over
Orlando City B, scoring one goal and being a constant threat throughout the match. On 14 April 2017, Flemmings scored his first goal of the season for New York, helping the club to a 3–1 victory over
Orlando City B. On 19 August 2017, Flemming scored two goals to help New York to a 4–0 victory over
FC Cincinnati. On 2 September 2017, Flemmings scored one goal and assisted on another in New York's 4–2 victory over
Tampa Bay Rowdies.
Tampa Bay Rowdies In January 2018, Flemmings signed with
Tampa Bay Rowdies in the USL.
Phoenix Rising Flemmings signed with
Phoenix Rising in 2019. He netted sixteen goals and seven assists in his first season with the team, and finished eighth in the league for the Golden Boot, finishing behind teammate and Golden Boot winner
Solomon Asante (22 goals). Flemmings' second season with Phoenix resulted in a Golden Boot Award, scoring 14 goals in a
COVID-shortened season. Phoenix was propelled to a first-place finish in Group B.
Homophobia controversy On 30 September 2020, while playing for the
Phoenix Rising, Flemmings was accused of using a Jamaican homophobic slur, "
batty boy", against the openly gay
San Diego Loyal midfielder
Collin Martin. Flemmings denied using the slur and said, in a
Twitter statement following the match, that he stands "in solidarity with the
LGBTQ+ movement". It was the last time that Flemmings took the pitch for Phoenix Rising. The USL Championship suspended him six games for using "foul and abusive language" and fined him an undisclosed amount. In addition, Phoenix Rising team officials placed Flemmings on administrative leave for the remainder of his contract with the team, which concluded on 30 November 2020. Flemmings' contract with the team was not renewed. The incident ultimately cost Rising a chance to host the USL Championship Final. Rising and
Louisville City FC both finished with 35 points and 11 wins, but Rising had a higher goal differential and would have thus had home-field advantage had it reached the final. However, Rising was only in contention to host the final as a result of the three points it earned by forfeit. Due to the ensuing outcry, Rising announced that if it reached the final, whoever won the Eastern Conference final would have home-field advantage in the Championship Final. They were set to play the
Tampa Bay Rowdies in Tampa Bay in that game, but it was canceled due to a COVID outbreak in the Rowdies organization.
Birmingham Legion On 13 January 2021, Flemmings joined USL Championship side
Birmingham Legion. In the announcement of Flemmings joining Legion, team officials noted his history with homophobia at Phoenix Rising, but said they believe that "second chances provide opportunities for growth." Team officials also said they had "extensive conversations" with Flemmings' former coaches and teammates, in addition to Martin and Donovan for their perspective on the team signing Flemmings. Flemmings also apologized for the incident in the statement. Toulouse was promoted to
Ligue 1 at the end of the 2021–22 season, but Flemmings did not make any appearances in the top tier during the first half of the 2022–23 season.
Loan to Niort On 31 January 2023, Flemmings was loaned to
Niort in
Ligue 2 until the end of the 2022–23 season. ==International career==