The 33rd Ryder Cup, also known as the "Battle of Brookline", was held September 24–26, 1999, in the United States at The Country Club in Brookline, Massachusetts, a suburb southwest of Boston.
The American team won the competition by a margin of 14 to 13, The Europeans, leading 10–6 heading into the final round, needed only 4 points on the final day to retain the cup. The Americans rallied on the Sunday, winning the first 6 matches of the day to surge into the lead. Further wins by Steve Pate and Jim Furyk took them into a 14–12 lead. The Americans recaptured the Ryder Cup when Justin Leonard halved his match with José María Olazábal. With the match all-square Leonard holed a 45-foot birdie putt on the 17th hole. After controversial premature celebrations on the green, Olazabal then missed his 22-foot birdie putt to leave Leonard one up with just one hole to play, assuring him of a half point and guaranteeing an American victory.
The behavior of both U.S. spectators and the U.S. team was criticized by both American and European media. U.S. spectators raucously heckled and abused European players. Allegations were also made regarding cheating on the part of course marshals. Notoriously, the U.S. team raucously invaded the 17th green after Leonard had holed his long putt but before Olazábal had attempted his shorter putt. The incident was viewed by many in both the US and Europe as appalling sportsmanship. Veteran broadcaster Alistair Cooke described the last day of the tournament as "a date that will live in infamy" in a Letter from America entitled "The arrival of the golf hooligan".
At the time, the American win was the largest final day come-from-behind victory in Ryder Cup history; Europe achieved the same feat in 2012. It is still widely regarded as one of the most impressive come-from-behind victories in recent sports history.
This was one of the last public appearances of Payne Stewart, who died in a plane crash less than a month later.
Pre-match comments
In the lead-up to the Ryder Cup, Payne Stewart said of the European team, "On paper, they should be caddying for us." Jeff Maggert echoed the sentiment in a press conference prior to the matches, saying, "Let's face it, we've got the 12 best players in the world." Colin Montgomerie declined to react, saying, "You want someone to bite. Well, I'm not going to."
The course
The Country Club, located in Brookline, Massachusetts, is one of the oldest country clubs in the United States. It was one of the five charter clubs which founded the United States Golf Association, and has hosted numerous USGA tournaments including the U.S. Open in 1913, won by then-unknown Francis Ouimet. The club is one of the largest of its kind in the northeastern U.S., with about 1300 members.
The club has two courses, but neither was used in its entirety for the Ryder Cup. The 18-hole Main Course, regularly played by club members, is essentially identical to the original 18-hole course completed in 1899 and used for the 1913 U.S. Open. The 9-hole Primrose Course was added in 1927. Major events that require a longer course, such as the Ryder Cup, use a layout most often known as the Championship Course, using 15 holes from the Main Course and replacing three with parts of the Primrose Course. Specifically, one hole of the Main Course is replaced by a composite hole that uses the teeing ground of the 1st Primrose hole and the putting green of the 2nd Primrose hole, and two holes from the Main Course are entirely replaced by the 8th and 9th holes of the Primrose Course.
Television
The 33rd Ryder Cup was covered live in the United States for all five sessions. USA Network covered the Friday action, with Bill Macatee and Peter Kostis in the 18th tower. The weekend was covered live by NBC Sports, with Dick Enberg and Johnny Miller in the 18th tower, Dan Hicks calling holes, and on-course reporters Gary Koch, Mark Rolfing, Roger Maltbie, and John Schroeder. Jim Gray conducted interviews, and on the final day was also used as a fifth on-course reporter. On the weekend, former European Ryder Cup captain Bernard Gallacher was brought in as a guest analyst to provide a European perspective.
In the UK, BBC and Sky Sports both had a presence, with Peter Alliss and Ewen Murray being the lead broadcaster for each with contributions from Butch Harmon, Bernard Gallacher, Peter Oosterhuis and Tony Jacklin.