The pair joined "Today" host Matt Lauer and a regular guy from Omaha, Neb., in a foursome bent on disproving Tiger Woods' theory that it takes a pro to beat the course.
Romo, who missed qualifying for the U.S. Open this spring, won with a 13-over 84. The beefy quarterback, who boasts a 2.2 handicap index, barely broke a sweat playing the first nine holes in 5-over 40 but slowed as the six-hour round wore on.
"It got really tough to stay sharp," he said, nodding toward the 18th hole, where he had his only double bogey after hitting into a bunker.
Timberlake, suffering from allergies, seconded Romo, although his game improved over the last four holes with two pars and two bogeys as he went into "Michael Jordan mode." A 6.0 handicap index, he parred the 18th to finish at 27-over 98.
"It's just inhuman, how well they strike it," he said, referring to Woods and his ilk.
Timberlake, outfitted in a dashing black trilby hat and tuxedo-stripe pants, started hamming it up with the gallery once his taut dancer's swing started to go south, blowing on the ball as it rimmed the seventh hole without any luck and asking the crowd to approve his drop into the rough at the edge of the fairway.
He couldn't blame his troubles on Mother Nature, either, after he skipped off the course after teeing off at the first hole and making a beeline for the men's room.
"Excuse me! I knew I forgot something," he called out to laughing spectators in his soft Tennessee drawl.
Lauer scraped by with a 100 on the par-71 course despite playing with a 6.2 handicap index. He came back from an early quad and a series of double bogeys to make a par 5 on the final hole.
"It's not easy," he said. "I didn't think Tiger made an outrageous statement."
The only one of the four who didn't seem to mind the scores was John Atkinson, a medical salesman from Omaha, Neb., who was chosen from 56,374 essay applicants to play in the challenge. He finished with a 43-over 114.