When Andy Roddick lost to Roger Federer at the U.S. Open last night, it was the continuation of an unfortunate trend for him. Roddick's career record against Federer now stands at 1-14, for a .066 winning percentage.

While this news must be disconcerting for Roddick and his fans, there are some baseball fans who feel a similar despair when their teams play a certain opponent.

In honor of Roddick's wretched record, here is a look at the 10 worst winning percentages in head-to-head match-ups in Major League Baseball history.

(Criteria: Records from 1901 through 2007, with a minimum of 162 head-to-head games, in the regular season only. Data from BaseballReference.com)

1) Tampa Bay Devil Rays: 54-109, .331 vs. New York Yankees

2) Tampa Bay Devil Rays: 56-107, .344 vs. Boston Red Sox

3) Texas Rangers: 226-351, .392 vs. Baltimore Orioles

4) (Tie) Kansas City Royals: 167-244, .406 vs. New York Yankees and Texas Rangers: 236-345, .406 vs. New York Yankees

6) (Tie) Oakland/Philadelphia/Kansas City A's: 755-100, .407 vs. New York Yankees and Seattle Mariners: 174-253, .407 vs. Oakland A's

8) St. Louis Browns/Baltimore Orioles: 825-1193, .409 vs. New York Yankees

9) Washington Senators/Minnesota Twins: 760-1088, .411 vs. New York Yankees

10) Philadelphia Phillies: 762-1087, .412 vs. New York/San Francisco Giants

As you can see, the Yankees have proven to be problematic for some teams to beat. Those teams aren't alone, though. The Yankees have a .567 all-time winning percentage.

In fact, they have a .500 or better record against nearly every Major League franchise. Both the Los Angeles Dodgers and Cincinnati Reds have a 2-1 record against the Yankees, representing the only two teams with a winning record against them in regular season match-ups.