Cummings, a point guard from Jacksonville, Florida, committed to play for Temple on September 4, 2010.[1] He averaged 18.1 points, 8.1 assists, 4.0 steals per game as a senior at Providence School, in addition to carrying a 4.0 grade point average. The Jacksonville Times-Union named him the high school boys basketball player of the year.[2] Cummings drew attention from Stanford, Miami (Fl.), and Boston College, but chose Temple because of their winning tradition.[3]
As a freshman, Cummings averaged 1.4 points and 0.8 rebounds in 6.3 minutes per game. He started versus George Washington and posted 2 points and an assist.[4]
Cummings played in 34 games as a sophomore, starting 32, and averaged 5.8 points, 1.9 assists, and 1.4 steals per game. He posted double-figures scoring in six games, including a season-high 15 points in a victory over Rhode Island.[4]
In his junior season, Cummings was a Second Team Philadelphia Big 5 selection. He averaged 16.8 points, a team-leading 4.6 assists and 1.5 steals in 34.4 minutes per game. He scored 31 points in a game against UCF.[4]
As a senior, Cummings was named to the First Team All-American Athletic Conference.[5] He missed a game against Cincinnati after suffering a strained muscle in his leg on January 10, 2015.[6] He led the team in scoring (14.8 points per game), assists (4.2 per game) and steals (1.9 per game). With 189 free throws made, he finished tied for second in school history in made free throws in a season. Additionally, Cummings completed his collegiate career 35th on Temple's all-time scoring list, and led the team to a 17-win improvement from the previous year, the highest in the nation. Temple reached the NIT semifinals.[7]
On April 29, 2016, Cummings left Rio Grande Valley and signed with Dolomiti Energia Trento of the Italian LBA for the rest of the season.[15] On May 4, he made his debut with Dolomiti Energia in a 73–70 loss to Juvecaserta Basket, recording 12 points, three rebounds and two steals in 18 minutes of the bench.[16]
On July 17, 2017, Cummings signed a 1+1 year deal with the Turkish club Darüşşafaka.[19] Cummings helped Darüşşafaka to win the 2018 EuroCup title.
2018–19 season
On July 6, 2018, Cummings signed with the German team EWE Baskets Oldenburg for the 2018–19 season. He got honored with the MVP title and lead his team to the 2nd place in the regular season.[20]
On August 11, 2023, Cummings signed with the South East Melbourne Phoenix in Australia for the 2023–24 NBL season.[24][25] On December 8, 2023, he was released by the Phoenix,[26] reportedly due to failing to meet off-court requirements on multiple occasions.[27] In 12 games, he averaged 14.5 points, 3.3 rebounds, and 2.7 assists per game.[27]