A native of Jamaica, Queens, in New York City, Clinkscales rose to prominence as a basketball player at a young age.

Although most of his statistics stagnated in his remaining years in college and his scoring average dropped, he led NCAA Division I in assist-to-turnover ratio as a senior.

After a three-year hiatus and one season in the American Basketball League with the Panama City Breeze, he began his NBL Canada career.

[2] At Shores Christian Academy, Clinkscales became a top player on the basketball team, averaging 21 points and 12 assists during his senior year.

[5] In another contest that month, Clinkscales notched 31 points and 11 assists in a triple-overtime loss to Gainesville High School, the top-ranked team at the Diamondback Challenge tournament.

[2][6] In the Florida Christian Athletic League's south quarterfinals, he had 40 points and 14 assists as his team beat Ocala Word of Faith by a 100–32 margin.

[6] Clinkscales's team won the National Association of Christian Athletes championship behind a 36-win season, and he was named the Ocala Star-Banner boys' basketball player of the year.

He was, however, in the spotlight playing for the Atlanta Celtics, an Amateur Athletic Union (AAU) program made up of players such as Dwight Howard, Josh Smith, and Randolph Morris.

[4] Basketball news website The Hoop Scoop named Clinkscales the 47th-best high school player in his class as he entered college.

[2] He made multiple unofficial visits to Florida State, which was his first choice;[10][11] however, the team did not offer him an athletic scholarship because of his low test scores.

[4] Blue Demons head coach Dave Leitao praised the new signee, saying, "Cliff is a true point guard who brings speed, athleticism, and quickness that we will need in our program.

"[6] On November 20, 2004, Clinkscales made his collegiate debut with the Blue Demons by scoring one point and recording two assists in 14 minutes against Bowling Green.

[34] Following an early loss at the 2007 National Invitation Tournament (NIT), he capped the season playing 12 minutes per game and averaging 1.4 points, 2.3 assists, and 1.2 rebounds per contest.

[37][38] Heading into late December, in the midst of multiple injuries to his teammates, Clinkscales played more and frequently appeared in the Blue Demons' starting lineup.

[43] On November 7, 2008, Clinkscales was selected as the seventh pick of the ninth round in the 2008 NBA Development League Draft by the Erie BayHawks.

[44] He made his official professional debut with the BayHawks on November 28, scoring 12 points to go along with four rebounds and three assists in a loss to the Fort Wayne Mad Ants.

[50] Head coach Clay Moser described Clinkscales' arrival as a boon to the team, saying, "We like Cliff's ability to get into the middle of the lane and create shots for others.

[58] After leaving the D-League, Clinkscales signed in 2013 with the Panama City Breeze of the semi-professional American Basketball League (ABL), with no indication that he joined any other team since his tenure with the BayHawks.

A local broker filed a civil lawsuit against Fisher to evict the players, and county sheriff deputies soon forced them to leave the house.

While living in the area, the players received aid from a local resident, Vonda Gainer, who they met at a Dollar Tree store.

[60] In February 2014, shortly after his time with the Breeze, Clinkscales joined the Halifax Rainmen of the National Basketball League of Canada (NBL) for the remainder of the 2013–14 season.

[66] On April 20, 2014, Clinkscales represented the Atlantic Division at the NBL Canada All-Star Game in Charlottetown, Prince Edward Island.

[68] On May 14, 2014, Clinkscales was announced as one of six protected players on the Rainmen roster for the upcoming season, meaning that he could not be approached by any other NBL Canada team.

[85] In the Hurricanes' regular season opener on Boxing Day 2015, Clinkscales added 13 points to help overcome the Moncton Miracles.

[100] Despite his previous claims, Clinkscales re-signed with the Hurricanes for the 2016–17 season on October 18, 2016, having been persuaded to make the decision by newly hired head coach Kevin Keathley.

[103] On December 26, in his season debut, Clinkscales scored six points, grabbed five rebounds, and passed for a team-high five assists to defeat the Moncton Miracles.

[110] For the second consecutive season, the Halifax Hurricanes lost to the London Lightning in the NBL Canada Finals, this time in a winner-take-all Game 7.

[123] Clinkscales has played streetball with the Sean Bell All-Stars against local teams in New York City, acting as the starting point guard.

[124] The Sean Bell All-Stars won the Trayvon Martin Invitational in August 2013, with a team that featured Clinkscales and Tobias Harris, in Harlem, New York.

"[125] In 2015, he competed for the All-Stars at The Basketball Tournament, in a team that featured Delroy James and Zamal Nixon and was managed by Raheem Wiggins.