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 and gamesmanship. 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.

Format The Ryder Cup is a match play event, with each match worth one point. The competition format used from 1991 to 2002 was as follows: Day 1 (Friday) — 4 four-ball (better ball) matches in a morning session and 4 foursome (alternate shot) matches in an afternoon session Day 2 (Saturday) — 4 foursome matches in a morning session and 4 four-ball matches in an afternoon session Day 3 (Sunday) — 12 singles matches With a total of 28 points, 14 points were required to win the Cup, and 14 points were required for the defending champion to retain the Cup. All matches were played to a maximum of 18 holes.

Teams Team Europe The 1999 European Team Points Table began in September 1998, and concluded on August 22, 1999, after the BMW International Open. The top 10 players in the Points Table qualified automatically for the team. Captain Mark James then left out the number 11 player Robert Karlsson and the experienced (but out-of-form) Bernhard Langer by instead selecting Andrew Coltart and Jesper Parnevik as the two 'wild card' players to round out the team.

 Team EuropeNameAgePointsrankWorldrankingPreviousRyder CupsMatchesW–L–HWinningpercentage Mark James 45 Non-playing captain Colin Montgomerie 36 1 3 4 18 9–6–3 58.33 Lee Westwood 26 2 5 1 5 2–3–0 40.00 Darren Clarke 31 3 21 1 2 1–1–0 50.00 Paul Lawrie 30 4 48 0 Rookie Miguel Ángel Jiménez 35 5 45 0 Rookie José María Olazábal 33 6 24 5 25 14–8–3 62.00 Sergio García 19 7 25 0 Rookie Jarmo Sandelin 32 8 73 0 Rookie Jean van de Velde 33 9 90 0 Rookie Pádraig Harrington 28 10 72 0 Rookie Andrew Coltart 29 12 66 0 Rookie Jesper Parnevik 34 15 15 1 4 1–1–2 50.00

Captains picks are shown in yellow; the world rankings and records are at the start of the 1999 Ryder Cup.

As vice-captains, European captain Mark James selected Ken Brown and Sam Torrance, to assist him during the tournament.

Team USA The 1999 U.S. Ryder Cup Team was chosen on the basis of points compiled by the PGA of America, early 1998, through the 81st PGA Championship, August 12–15, 1999. Points were awarded for top-10 finishes at PGA Tour co-sponsored or sanctioned events, with added emphasis on major championships and events played during the Ryder Cup year. The top 10 finishers on the points list automatically qualified for the 12-member team, and U.S. Captain Ben Crenshaw selected the final two players—Steve Pate and Tom Lehman.

 Team USANameAgePointsrankWorldrankingPreviousRyder CupsMatchesW–L–HWinningpercentageBen Crenshaw 47 Non-playing captainTiger Woods 23 1 1 1 5 1–3–1 30.00David Duval 27 2 2 0 RookiePayne Stewart 42 3 8 4 16 8–7–1 53.12Davis Love III 35 4 4 3 13 5–8–0 38.46Mark O'Meara 42 5 11 4 12 4–7–1 37.50Hal Sutton 41 6 10 2 9 3–3–3 50.00Justin Leonard 27 7 12 1 4 0–2–2 25.00Jim Furyk 29 8 14 1 3 1–2–0 33.33Phil Mickelson 29 9 13 2 7 4–1–2 71.43Jeff Maggert 35 10 16 2 7 4–3–0 57.14Tom Lehman 40 12 23 2 7 3–2–2 57.14Steve Pate 38 14 28 1 2 0–1–1 25.00

Captains picks are shown in yellow; the world rankings and records are at the start of the 1999 Ryder Cup.

As vice-captains, United States captain Ben Crenshaw selected Bruce Lietzke and Bill Rogers, to assist him during the tournament.

Friday's matches Morning foursomes Paul Lawrie hit the opening tee shot to begin the 33rd Ryder Cup Matches. The Americans got off to a good start when Tom Lehman chipped in at the first hole, but the matches quickly swung toward Europe's favor. With the Americans' top two pairings losing, the Europeans gained confidence, finding a dynamic duo in Jesper Parnevik and Sergio García.

Results Montgomerie/Lawrie 3 & 2Mickelson/DuvalGarcía/Parnevik 2 & 1Lehman/WoodsJiménez/HarringtonhalvedLove III/StewartClarke/Westwood 3 & 2Maggert/Sutton 2 Session 1 2 Overall 1

Afternoon four-ball Lee Westwood and Darren Clarke defeated Tiger Woods and David Duval, the top two players in the world rankings. Woods missed a short eagle putt at the 14th that would have squared the match, while Westwood hit a fantastic chip shot at the final hole to secure victory. Both Duval and Woods were shut out on day one.

The day's best match, and arguably the best team match of the week, pitted Parnevik and García against Phil Mickelson and Jim Furyk. Parnevik holed out for eagle at the par-4 eighth, putting him and García a combined 6-under-par for the match, but just 1 up. At the 13th, Furyk chipped in from near a pond to square the match, giving the American fans a chance to go into a frenzy. At the next hole, Garcia pitched in for an eagle from just the right of the green at the par 5, putting Europe back in front. At the 16th hole, with the Americans 1 down, Mickelson hit his tee shot inside of four feet from the hole. He was left with the short putt to square the match, but missed it, and the Americans continued to trail. At the final hole, Mickelson again put the ball within five feet of the hole, but again missed the putt, leaving the Americans with an agonizing 1 down loss, and keeping Parnevik and García unbeaten.

Results Montgomerie/LawriehalvedLove III/LeonardGarcía/Parnevik 1 upMickelson/FurykJiménez/Olazábal 2 & 1Maggert/SuttonClarke/Westwood 1 upDuval/Woods 3 Session 6 Overall 2

Saturday's matches Morning foursomes Tiger Woods won his first match of the week, teaming with new partner Steve Pate. Woods eagled 14 while Pate hit a shot from the rough at the 18th to within 15 feet to secure the win over Pádraig Harrington and Miguel Ángel Jiménez.

Jesper Parnevik and Sergio García won their third straight match, dominating the back nine to handily beat Justin Leonard and Payne Stewart.

The final match on the course pitted Jeff Maggert and Hal Sutton against Colin Montgomerie and Paul Lawrie. Maggert took the match into his hands in the final holes, making a long birdie putt at 17 to put the Americans in front, then sealing the win by hitting his approach within 5 feet at the final hole.

Results Montgomerie/Lawrie 1 upSutton/MaggertClarke/Westwood 3 & 2Furyk/O'MearaJiménez/Harrington 1 upWoods/PateParnevik/García 3 & 2Stewart/Leonard 2 Session 2 8 Overall 4

Afternoon four-ball With the Americans desperate to climb back into the contest, Captain Ben Crenshaw changed up some pairings in hope of making up at least two points. After playing with Maggert during the first three sessions, Sutton teamed with Leonard, but could only produce a half against the Spanish duo of Miguel Ángel Jiménez and José María Olazábal.

Woods and Pate played together again, facing Montgomerie and Lawrie. Pate chipped in for birdie at the first hole, just as Lehman had done the day before, also while playing with Woods. However, the world #1 missed key putts on the back nine and lost for the third time in four matches.

Phil Mickelson finally found his game, nearing holing out for eagle at the 10th, as he and Tom Lehman defeated Lee Westwood and Darren Clarke.