It was the first time the British Open had qualifying around the world in an effort to give more players a chance to play golf's oldest championship.
Montgomerie was among a dozen players competing for six spots in a sudden-death playoff, and he got in after the second hole. It was a rare bright spot for the former world No. 2, who is going through a divorce and has slipped out of the top 50 in the world for the first time in over a decade.
'It's the first decent thing that has happened to me for a while,' said Montgomerie, who earned one of 17 spots available in the European tour qualifier.
Among those who failed to qualify were former Masters champions Bernhard Langer, Jose Maria Olazabal and Ian Woosnam, along with Justin Rose and Jesper Parnevik.
Donald, who plays the PGA Tour on a regular basis, gave his fledgling Ryder Cup hopes a boost by qualifying at Congressional in Bethesda, Md.
The PGA Tour qualifier had 120 players, but only 68 showed up. Royal & Ancient officials said they would investigate why there so many no-shows, and those players could be banned from playing next year.
'It is disappointing, and we will have to analyze who has withdrawn and why they have done so,' R&A championship director David Hill said. 'Anybody who withdraws has to have a good reason, and if not the championship committee can take whatever action they feel appropriate.'
Mathias Gronberg holed a bunker shot for eagle on No. 10, sending him to a 31 on the back nine of the famed Blue Course at Congressional to share medalist honors with Carl Petterson and Spike McRoy at 9-under 134.
Others who qualified at Congressional were former PGA champion Steve Elkington; Rod Pampling; Bo Van Pelt; Matt Goggin; Tim Herron; Hunter Mahan; Aaron Baddeley; Skip Kendall; Glen Day; Bob Estes; and Cameron Beckman.
Jeff Maggert, coming off a third-place finish at the U.S. Open and 10th in the Ryder Cup standings, and former PGA champion Mark Brooks withdrew when it was clear they would not qualify.
At Sunningdale, Mark Foster, Paul Broadhurst and Nicolas Colsaerts shot 9-under 134 to share medalist honors.
Montgomerie, a seven-time Order of Merit winner in Europe, missed the U.S. Open because his ranking was too low and risked missing the British Open for the first time since 1989. He now has high hopes for Royal Troon, where his father was the longtime club secretary.
'Now I should have a realistic chance,' he said. 'I know every blade of grass there.'
Others who qualified were Paul McGinely; Kenneth Ferrie; Euan Little; Simon Wakefield; Miles Tunnicliff; Christian Cevaer; Klas Eriksson, Gary Emerson, Eduardo Romero; Marten Olander; Peter Hedblom; Maarten Lafeber; and Warren Bennett.
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