Flemmings transferred to University of North Carolina at Wilmington following his sophomore season at Barton after his mother, Tracy Flemmings, convinced new head Seahawks coach Kevin Keatts to offer him a spot on the team as a walk-on. After sitting out one season due to NCAA transfer rules, Flemmings immediately entered the Seahawks' starting lineup and lead the team with 16.2 points and 5.8 rebounds per game and was the first walk-on to be named first team All-Colonial Athletic Association. Additionally, he was named the Most Outstanding Player of the 2016 CAA Men's Basketball Tournament as the Seahawks clinched their first NCAA Tournament appearance in ten years. He scored 18 points in 39 minutes in UNCW's first round loss to fourth-seeded Duke in the 2016 NCAA Tournament. Following the end of the season, Flemmings was awarded a scholarship for his senior year. As a redshirt senior, Flemmings was again named first team All-CAA after averaging 15.8 points, 5.6 rebounds, 2.2 assists and 1.4 steals per game as the Seahawks won the CAA regular season and conference tournaments for the second straight year. In his final career game, Flemmings scored 18 points with 9 rebounds and 4 assists against nationally ranked Virginia in the 2017 NCAA Tournament.
Flemmings was selected 7th overall in the 2017 NBA G League draft by the Reno Bighorns and subsequently traded to the Maine Redclaws on draft night. He was cut by the Redclaws at the end of the preseason and was claimed from the player pool by Raptors 905 on November 15, 2017. He was waived by the team on November 27, 2017 after appearing in only four games, averaging 0.8 points per game.
Flemmings signed with ETHA Engomis of Cyprus Basketball Division A on September 6, 2018. He averaged 16.4 points, 5.6 rebounds, 1.8 assists and 1.1 steals over 24 games and was named Rookie of the Year, 3rd team All-Cyprus League, and All-Import team by EuroBasket.com.
Following the end of the Division A season, Flemmings signed with Peristeri of the Greek Basket League on May 2, 2019 for the last game of the GBL season and the subsequent play-offs.
On November 11, 2019, he signed with Vilpas Vikings of the Korisliiga. Flemmings averaged 10.8 points, 4.0 rebounds, 1.1 assists and 1.5 steals in 12 games before leaving the team.
Flemmings signed with BK Levickí Patrioti of the Slovak Extraliga on January 20, 2020.
Personal
Flemmings’ mother, Tracey, played basketball collegiately at Barber–Scotia College and was an all-conference selection at guard. His father, Charles, also played college basketball at Knoxville College and received offers to play professionally overseas. Flemmings’ sister, Candace, was a collegiate rower for the University of Tennessee.