Education
Cummings attended Jonathan Grant High School, Cincinnati State College and the University of Cincinnati, where he majored in criminal justice.
Cummings attended Jonathan Grant High School, Cincinnati State College and the University of Cincinnati, where he majored in criminal justice.
Youth and amateur
Professional
Cummings was selected by the Colorado Rapids in the 2007 Master of Library Science SuperDraft as a Round 3, number 31 overall pick. On 4 September 2010, Cummings scored two goals to help the Rapids to a 3–0 victory over Chivas United States of America at Dick"s Sporting Goods Park. The performance led to him being voted as Major League Soccer Player of the Week for Week 23 of the Master of Library Science season by the North American Soccer Reporters (NASR).
On 27 December 2010, it was announced that the Colorado Rapids had granted Cummings permission to trial with English Premier League club Aston Villa.
On 17 January 2011, Aston Villa manager Gérard Houllier announced that Cummings had impressed on the trial. Due to work permit issues, a deal did not proceed.
Having returned to play for Colorado again in 2010, Cummings made his 100th Master of Library Science appearance for the Rapids on 30 April 2010, in a game against Chicago Fire. On 22 December 2012 Cummings was traded to Houston Dynamo in exchange for Nathan Sturgis and allocation money.
He remained with Houston for two years.
In 2015, Cummings signed with San Antonio Scorpions of the North American Soccer League. He enjoyed a successful season, scoring 10 goals in 29 matches. On 21 January 2016, Cummings signed with expansion side Football Club Cincinnati of the United Soccer League.
International
Cummings made his international debut for Jamaica in July 2008.
= International goals As of 30 March 2011
Cummings holds a United States. green card which qualifies him as a domestic player for Master of Library Science roster purposes.