On December 2, D.C. United announced it would not exercise options on the contracts of defenders Barry Rice and Juan Manuel Peña, as well as midfielder Carlos Varela and Brandon Barklage.

[21] During the first week of February, rumors began to circulate that D.C. United was in "serious talks" with FC Sochaux-Montbéliard to acquire U.S. national team forward Charlie Davies on loan from the French Ligue 1 side.

[24] Subsequently, club public relations released a press statement declaring that Davies would join United on loan if they saw him match fit.

[33] Following training in Florida, United continued their preseason tour by traveling to Southern California, where they played against the PDL's Ventura County Fusion, as well as a match against UC Santa Barbara's men's team.

Brettschneider's tenth-minute tally was the lone goal of the match, thus giving United a 2–0–0 record in the tournament table, and placing them in a key position to win the entire cup.

The club closed out their cup run with their third and final match against last-place Toronto FC;[35] who had fallen to both Chicago and Charleston earlier in the week.

[35] Towards the end of the first half, nearing the halftime break, came an unusual string of reckless challenges from Toronto right back, Mikael Yourassowsky, on loan from Croatian side Rijeka.

During the summer, with United only losing three matches, and either winning or drawing their other league fixtures, the club ascended in the standings and eventually, into a position that offered a berth into the wildcard round of the playoffs.

In the 67th minute of play, the United leveled the score thanks to a strike from Santino Quaranta.The tie was short-lived, as the Rapids immediately struck back with a 68th-minute goal from Scottish-international Jamie Smith.

United equalized late into match, in the second minute of stoppage time, thanks to a Charlie Davies penalty kick, his fourth in MLS league play and his fifth with D.C.

[48][49] The most questionable calls were associated the severity of cards distributed to players and a late-match decision to award a penalty kick to the United, in which many claimed was a fake trip in the box.

The goal received much national attention from the controversy surrounding the decision to award a penalty, and Davies' celebration for successfully converting the kick.

[49] Subsequent to the match, center referee Abiodun Okulaja ejected Galaxy midfielder Jovan Kirovski for cursing at him while sniping his decision.

[51] The opening goal was scored by Chris Pontius, which was his first in MLS league play since his hat trick against Seattle Sounders FC last June, prior to his calf injury.

Additionally, the game saw United not only pull out their first away win of the season, but their first shout-out since the Carolina Challenge Cup; which was also Bill Hamid's first shutout in MLS play.

In the 39th minute, United defender Marc Burch scored off a complex free kick that caused the Dynamo defense to scramble, tallying his first goal of 2011.

Bošković, who left in the team's U.S. Open Cup qualifier loss to New England,[62] was revealed to have a torn Anterior cruciate ligament (ACL) in his right thigh.

In the 56th minute, what seemed to be a certain foul in the box for a penalty from Colorado's Jeff Lorentowictz on D.C.'s Joseph Ngwenya was waved off, resulting in heavy dissent from both the players and the bench of United.

Heading into Memorial Day Weekend, United wrapped up May with the opening match of their two-game West Coast road trip on May 29 at Jeld-Wen Field to take on the Portland Timbers.

While United were able to hold the 1–0 lead well into the second half of play, a chain of contentious decisions from center official Geoff Gamble, but primarily linesmen Eric Proctor.

As the international transfer window neared, United made an unanticipated, blockbuster trade with their Atlantic Cup rivals, New York Red Bulls on June 27.

In spite of the strong finish at Los Angeles, who led the Western Conference and overall standings at the time, United failed to win any matches during the month of June, amassing three subsequent draws and a loss.

Met with heavy jeers at Rio Tinto, Davies successfully bagged the match tying goal, in spite of the fact that Salt Lake's goalkeeper, a former United player, Nick Rimando, guessed the correct way.

However, Najar's free kick was successfully passed to Pontius, whose shot deflected off the crossbar, allowing the match to remain leveled at one apiece.

[79] That same day, the club made more headlines when they announced that Fred would be allowed to join Australian A-League side, Melbourne Heart on a summer transfer in July.

The match, ending in a 2–2 tie saw newcomer Dwayne De Rosario make an assist to Josh Wolff as well as midfielder Andy Najar score a long range volley from 35 yards.

The Red Bulls, previously thrashed United 4–0 in April, and looked to be heavy favorites by fans and the media alike, especially coming off a 5–0 home win over Toronto.

Upon their homestance against the Canadian teams, United hit the road for matches at Eastern Conference rivals, Chicago Fire and Sporting Kansas City.

On September 6, United players and staff rejoined one another in training, four days ahead of their trip to Los Angeles for their road fixture against Chivas USA.

The slight goal lead seemed certain to return United back into a playoff position for only Chicago's Sebastián Grazzini and Diego Cháves to score for the Fire in the third and fifth minutes of stoppage time, respectively.