During the 2006 MLS season, Boswell was the starting centerback for DC United, who finished the with the best regular season record and won the Supporters' Shield. Boswell was named an All-Star, and he started and played the entire All-Star match in the 1-0 victory over Chelsea, the defending English Premiership champions. He was named DC United's 2006 Defender of the Year and Humanitarian of the year. He was also named the 2006 MLS Defender of the Year and selected as a member of the Best XI.
As a child, Boswell appeared on the Nickelodeon TV show GUTS as Bobby "Lightning" Boswell. At one point, he struggled to kick a soccer ball placed on a pedestal into a goal, missing the ball repeatedly, but still ended up winning the event. Bobby is the son of Susan and Charles "Ted" Boswell, also related to Allan "David" Boswell, and William "Tad" Boswell, along with the rest of Tad's children, Brad and Sabrina Boswell. His older brother, Billy, also played soccer at FIU. Their cousin is "Frasier" actor Adam Blake Boswell
In 2007, Bobby launched his personal web site, http://www.bobbyboswell.com.
On December 11, 2007, D.C. United traded Bobby to the Houston Dynamo in exchange for goalkeeper Zach Wells.