The match pitted the political rivals against Vice President Joe Biden and Ohio's Republican Gov. John Kasich. The match was won on the 18th hole, with the winning partners each pocketing a $2 prize.
The question now is whether a partnership forged on the tees, fairways and greens of a military base course can yield success in the policy arena. Obama and Boehner find themselves on opposite sides of everything from deficit reduction to the military campaign in Libya.
Aides to both men played down the chances of deals being struck on the par-72 East Course at Joint Base Andrews, but acknowledged the outing could improve a relationship that is respectful, but hardly close.
Tee time for the foursome was 9:30 a.m. at Obama's home course at the base outside Washington.
The White House made a rare exception and allowed the press to watch Obama and his playing partners finish the first hole, a par five.
Biden was cool under pressure, sinking a 15-to-20 foot putt.
"Did you all catch that?" Obama shouted to reporters gathered near the green.
The president, dressed in dark pants, a white polo shirt and a baseball cap, putted for par, tapping him a short shot after missing a 12-footer.
Kasich, a former congressman, missed a long 30-footer, then tapped in for par. Boehner, one of the best golfers in Congress, gave a hearty "Oh yeah!" after draining a short putt.
Obama, who is not in Boehner's links league, patted the speaker on the back as they headed toward the second hole, the president driving their cart.
After wrapping up the match, the foursome headed to the clubhouse, where they had a cold drink and talked with service members. They also caught some action at the U.S. Open, the professional tournament going on in suburban Maryland.
While Obama is an avid golfer, he rarely plays with anyone outside of his small cadre of close aides. His rounds run long, usually well over five hours, and those close to the president say he revels in the chance to get out of the spotlight.
Obama's penchant for privacy extends to his social life. He surrounds himself with a tight inner circle of family and friends, and rarely socializing with other politicians in Washington. In fact, Saturday's golf outing was one of the first time Obama and Boehner have gotten together for anything other than a policy meeting.
White House spokesman Jay Carney said earlier in the week that the outing was "meant to be an opportunity for the speaker and the president, as well as the vice president and Ohio governor, to have a conversation, to socialize in a way that so rarely happens in Washington."
The Obama-Boehner golf outing coincided with White House and congressional negotiations on a long-term deficit reduction plan and raising the government's borrowing authority. Republicans have insisted on significant cuts of about $2 trillion over 10 years or 12 years before agreeing to increase the current $14.3 debt ceiling, which the government says it will surpass Aug. 2.
While aides for both men tried to lower expectations that deal on the deficit -- or anything else, for that matter -- would be reached on the course. But it couldn't hurt.
"It may move you a little bit closer toward the kind of compromise that we need to get the things done that the American people expect us to get done," Carney said. "If it takes a few hours out on the golf course to help that process, I think it's a worthwhile thing to do."