D.C. United's road back to the MLS playoffs -- should it clinch a spot Saturday against Columbus -- has been a painful one. Here are United's worst moments since it was last in the postseason in 2007:

5. Oct. 15, 2011: Chicago 2, D.C. United 1 » After a 90th-minute penalty kick from Dwayne De Rosario put United in front, a ragged defense allowed two stoppage responses from the Fire as United dropped its fourth game in a row.

4. Oct. 4, 2008: Chivas USA 3, D.C. United 0 » Part of 10 losses in 14 matches in all competitions to end the season, this date also saw high-priced Marcelo Gallardo's disappointing spell in Washington end with a knee injury. Afterward, owner Victor MacFarlane said, "Not only are we bad, but we paid to be bad."

3. Oct. 3, 2009: Chivas USA 2, D.C. United 0 » United's first ever three-game losing streak at home culminated with the RFK Stadium crowd calling for coach Tom Soehn's head. But the "Fire Soehn" chant started after Ben Olsen had already been red-carded in the 65th minute to seal the result.

2. Aug. 4, 2010 » First-year coach Curt Onalfo was fired. Brought in when United failed to persuade Caleb Porter to leave Akron, Onalfo presided over a 1-8-0 start that included seven shutout defeats. It was the first time in United's history that a coach was dismissed in midseason.

1. Oct. 23, 2010: Toronto 3, D.C. United 2 » United legend Jaime Moreno earned and converted a penalty kick in his final MLS match, but the worst season in franchise history ended with goals from players who are now on the roster: Maicon Santos and De Rosario, who scored twice in the second half.

- Craig Stouffer