On August 16, 2004, Jenkins became the first African American to win the singles title of the USTA Junior Hard Court Games at the age of 17.
In 2005 Jenkins took part in the US Open and won the game against the Swiss George Bastl . In the second match he was defeated by the Spaniard Rafael Nadal in an exciting encounter . In 2006, Jenkins narrowly missed qualifying for Wimbledon when he lost to Joshua Goodall in a match with three tie-breaks . At the 2007 US Open , Jenkins had to play in the first round against world number one and defending champion Roger Federer , against whom he had no chance with 3: 6, 2: 6, 4: 6.
Jenkins played his last professional match in February 2010 in San José , where he lost to fellow countryman Ryler DeHeart in the first round of qualifying . He has not been in the world rankings since January 2011.