Douglas-Roberts played high school basketball at Cass Technical High School and Northwestern High School. He played for Cass Tech in 2003 and 2004 averaging 28 points, 10 rebounds and six assists. After the 2004 season he transferred to Northwestern where he saw limited time due to transfer rules and didn't join the team until the second semester. He finished the season averaging 13.8 points and 5.4 rebounds per game. Considered a four-star recruit by Rivals.com, Douglas-Roberts was listed as the No. 26 shooting guard and the No. 75 player in the nation in 2005.
College career
During his freshman season he played in 34 games starting 25. He finished the season averaging 8.3 points, 3.3 rebounds, and 1.5 assists per game. Because of his great play he was on the Conference USA All-Freshman Team. During his sophomore season he started all 35 games he played in. He led the Tigers with 15.4 points per game and received many honors including All-Conference USA first team and Associated Press All-America honorable mention among others. During his junior year, he helped the Tigers reach the 2008 NCAA Tournament, averaging 23.3 points over six games as the Tigers finished in second place, losing in the National Championship game to the Kansas Jayhawks 75–68 in overtime. In the last 1:15 of regulation in the game, Douglas-Roberts became a key factor in the team's loss, by missing a jump shot and three free throws, which helped allow Kansas to tie the game. At the end of the season he earned first-team All-American honors. He finished his college career with 1,545 points.
Professional career
NBA
On April 18, 2008, Douglas-Roberts announced that he would be declaring for the 2008 NBA draft. He was selected by the New Jersey Nets with the 40th overall pick, and on July 9, 2008, the Nets officially signed him. On June 25, 2010, Douglas-Roberts was traded by the Nets to the Milwaukee Bucks for a 2012 second-round draft pick.
Italy
In September 2011, Douglas-Roberts joined Virtus Bologna of Italy.
Second NBA stint and D-League
On October 1, 2012, Douglas-Roberts signed with the Los Angeles Lakers, but was waived on October 22. On October 27, Douglas-Roberts signed with the Dallas Mavericks along with center Melvin Ely, however, the two were waived the next day. On November 1, 2012, he was acquired by the Texas Legends of the NBA D-League. On December 23, 2012, he re-signed with the Dallas Mavericks. On January 6, 2013, he was waived by the Mavericks. In July 2013, Douglas-Roberts joined the Los Angeles Lakers for the 2013 NBA Summer League. On October 2, 2013, he signed with the New York Knicks. However, he was later waived by the Knicks on October 25, 2013. In November 2013, Douglas-Roberts was re-acquired by the Texas Legends. On December 11, 2013, he signed with the Charlotte Bobcats. On April 14, 2014, he hit a buzzer-beater to lift the Bobcats over the Atlanta Hawks, 95–93. On September 3, 2014, Douglas-Roberts signed with the Los Angeles Clippers. On January 15, 2015, Douglas-Roberts was acquired by the Boston Celtics in a three-team trade also involving the Phoenix Suns. Three days later, he was waived by the Celtics. On September 18, 2015, Douglas-Roberts signed with New Orleans Pelicans. However, he was later waived by the Pelicans on October 23 after appearing in five preseason games. On February 29, 2016, he was reacquired by the Texas Legends. He is currently the CEO and president of DCTG Media Agency.
NBA career statistics
Regular season
Playoffs
Personal
Douglas-Roberts has multiple tattoos on his neck and arms. One on the side of his neck is of his mother, one on the back of his neck has his initials, and one on his arm has verses 1–3 of from the Bible. He taps the arm tattoo three times before shooting a free throw. Douglas-Roberts suffered a retina tear in his eye during the 2010–11 pre-season. He began wearing protective eyewear after the surgery.