Bandon Trails; Bandon, Ore.
14th hole, 325 yards
Bill Coore and Ben Crenshaw’s fiercely debated two-shotter is our only 21st-century entry. The elevated tee shot plays to a wide, severely left-to-right sloping fairway. Play safely right and birdie is out of the equation. Reward awaits those who shorten the approach and play left to the tiny skyline green, which Coore was prepared to rebuild. But owner Mike Keiser disagreed. “It’s my favorite hole,” he said.

The Belfry (Brabazon); Sutton Coldfield, England
10th hole, 311 yards
At the 1985 Ryder Cup, captain Lee Trevino ordered his players to lay up instead of going for the boomerang-shaped green guarded by trees and a creek. The Americans bickered over the strategy and lost the Matches. The quarrelling—then and since—proves that this hole is a match-play gem.

The Country Club (Composite); Brookline, Mass.
4th hole, 338 yards
Driveable with a tiny green hidden over a small hill, the percentage play is to lay up to the generous fairway and wedge on. But for most, the temptation is just too great to drive near the putting surface because the hole looks so inviting.

The Course at Yale; New Haven, Conn.
4th hole, 437 yards
C.B. Macdonald and Seth Raynor blended the “Cape” and “Road” holes, providing a tempting (and ill-advised) option of driving over the inlet and shortening the approach. Trees left add to the trouble, but flirting with them opens a nice view to the green. The second shot was even more harrowing before the greenside “Road” hole bunker’s renovation.

National Golf Links of America, Southampton, N.Y.
17th hole, 460 yards
“Alps” features an angled bunker off the tee that rewards a drive down the right. Driving too safely left leaves an all but impossible approach to a green behind a hill. No matter the angle, the approach shot is blind, adding excitement to the stroll to the green.

Pine Valley Golf Club; Pine Valley, N.J.
13th hole, 486 yards
Along with the pine barrens and trees, the heroic second shot to the peninsula-perched green makes this ideal for matches. There is the option to go directly at the hole, try a right-to-left run up shot, or play well out to the right and pitch on to the undulating putting surface. Each option has risk, and so much depends on what your opponent does.

Riviera Country Club; Pacific Palisades, Calif.
10th hole, 311 yards
An iron off the tee rarely makes worse than par, yet the hole still lures pros into going for the well bunkered green, an approach that brings double bogey into play. As Jim Murray wrote, “This is a shameless little harlot that just sits there at the end of the bar in her mesh stockings and miniskirt and winks at you.”

Royal Melbourne Golf Club (West); Melbourne, Australia
10th hole, 305 yards
For decades this hole has tempted good players to do unwise things, always the mark of a great match-play hole. A dogleg left that plays to a tiny green set atop a hill, with severe penalty awaiting both long and short of the putting surface. Lay up and face an obstructed view. Go for the green and bring trouble into play.