Following are the first round pairings for the 2009 MLS Playoffs.
2009 MLS Playoffs
Eastern Conference:
Columbus Crew (#1 East) vs. Real Salt Lake (#5 West)
Chicago Fire (#2 East) vs. New England Revolution (#3 East)
Western Conference:
Los Angeles Galaxy (#1 West) vs. Chivas USA (#4 West)
Houston Dynamo (#2 West) vs. Seattle Sounders (#3 West)
All-Time Columbus Playoff Opponents
| Year | Round | Opponent | Result |
| 1996 | Quarterfinals | Tampa Bay Mutiny | Lost in 3 games |
| 1997 | Quarterfinals | Tampa Bay Mutiny | Won in 2 games |
| Semifinals | DC United | Lost in 2 games | |
| 1998 | Quarterfinals | New York Metrostars | Won in 2 games |
| Semifinals | DC United | Lost in 3 games | |
| 1999 | Quarterfinals | Tampa Bay Mutiny | Won in 2 games |
| Semifinals | DC United | Lost in 3 games | |
| 2000 | Did Not Qualiify | ||
| 2001 | Quarterfinals | San Jose Earthquakes | Lost in 2 games |
| 2002 | Quarterfinals | San Jose Earthquakes | Won in 2 games |
| Semifinals | New England Revolution | Lost in 3 games | |
| 2003 | Did Not Qualify | ||
| 2004 | Quarterfinals | New England Revolution | Lost in 2 games |
| 2005 | Did Not Qualify | ||
| 2006 | Did Not Qualify | ||
| 2007 | Did Not Qualify | ||
| 2008 | Quarterfinals | Kansas City Wizards | Won 2-leg series |
| Semifinals | Chicago Fire | Won 1-game series | |
| MLS Cup Final | New York Red Bulls | Won 1-game series | |
