The Benny Awards continue ever onward, and to day its time to give the Bobby Award, given to the team's most improved player. It's named for once and current D.C. United defender Bobby Boswell, who went from an undrafted rookie to Defender Of The Year in just a two-year stretch. Past winners include Taylor Kemp, Chris Korb, and Ethan White.
- Kofi Opare: Acquired via trade in the middle of last year, Opare spent the end of last year and the beginning of this year as one of United's Concacaf Champions League center backs. However, he really came to life this year when Steve Birnbaum was injured, pairing with Bobby Boswell and seamlessly keeping the defense running.
- Conor Doyle: After struggling to find the right position for him, the team finally found it this year: defensive forward/winger. The team needs other players to score goals, that isn't Doyle's job at this point; his job is to shut down a game after United has the lead. He was among the team leaders in tackles and aerials won, and was actually able to put in more crosses and through balls this year from the wing. Also, Doyleazo!
- Miguel Aguilar: The team's first round draft pick, he went from playing for the Richmond Kickers, to staring for the team in the Conacaf Champions League, to making the bench down the stretch for the team and being a substitute in both legs of the Conference Semi-finals.
- Taylor Kemp: Kemp improved his offense last year, becoming a certifiable weapon; this year, he improved his defense, coming up from a below-average defender with above-average offensive skills. If he can keep this progression up, he could join the upper-tier of MLS fullbacks in the next year or two.