Brookline, Massachusetts, August 27, 2025
News Summary
The 1999 Ryder Cup at The Country Club in Brookline is celebrated for its intense drama and memorable moments, including Tiger Woods’ pivotal win over Andrew Coltart. Despite Europe leading 10-6 after two days, the U.S. made a stunning comeback on the final day, winning 8.5 points and ultimately claiming the trophy with a score of 14.5-13.5. Controversial crowd behavior and key shots, like Justin Leonard’s clutch putt on the 17th, have marked this event as a significant chapter in golf history.
Brookline, Massachusetts — A Flashback to the Wild 1999 Ryder Cup
Golf fans love a comeback, and few turnarounds are talked about more than the one at The Country Club in Brookline. The 1999 Ryder Cup — often dubbed the Battle of Brookline — served up drama, controversy and a late-day surge that still gets pulses racing. A recent social media clip showing a young Tiger Woods beating Andrew Coltart 3&2 in their singles match brought that Sunday back into the spotlight.
How the scoreboard read before the storm
Europe looked in control through the first two days, holding a 10–6 edge heading into Sunday. If you were watching, you’d have felt the momentum swinging in their direction. But Sundays in match play can flip the script — and that’s exactly what happened here.
The American charge
The U.S. team put together an extraordinary final-day performance, winning 8.5 points in the singles to snatch the cup with a final score of 14.5–13.5. Among the many turning points was a dramatic putt on the 17th hole by Justin Leonard, a moment that people still call one of the most memorable clutch shots in Ryder Cup history. Tiger’s win over Coltart closed out on the 16th hole, and his point was a vital piece of the comeback.
Spotlight on the Coltart match
For Andrew Coltart, the event was his first Ryder Cup. He found himself up against a player who by 1999 was already a major star in the game, and the match finished on the 16th. That result helped feed the whirlwind that carried the U.S. to victory.
Controversy in the stands and on the turf
The week was noisy for reasons beyond the golf. Crowds were rowdy, and heckling became a serious issue — so much so that one player’s father walked off the course during play rather than endure the abuse aimed at his son. Moments of sportsmanship still shone through; one veteran competitor conceded a putt in the face of the poor behavior in the crowd, and that act was highlighted as a classy counterpoint to the hostility. A seasoned broadcaster later described the final day as infamous, and many fans and players still call the 1999 Ryder Cup one of the most controversial in golf history.
Where Tiger stood then and where he stands now
By the time of that Brookline showdown, Tiger Woods had been a professional for a few years and was already a major figure in golf. His career totals, according to records, list 82 PGA Tour victories and 15 Major Championships, including five Masters and four PGA Championships. His achievements earned him a place in the World Golf Hall of Fame in 2021.
Captaincy chatter and the road to 2025
In 2024 there were reports that Woods was in talks about captaining Team USA for the 2025 Ryder Cup, which is set for Bethpage Black. Conversations took place with the PGA of America’s leadership, but he ultimately stepped away from consideration shortly before any official announcement. At the time he withdrew, questions surrounded his health and current form, and he indicated he would consider leading the team only if the role’s demands were reduced. Meanwhile, Team Europe heads into the next match as defending champions after winning in Rome in 2023.
Why the 1999 Ryder Cup still matters to fans
The mix of intense rivalry, controversial crowd behavior, dramatic shots and landmark singles results makes Brookline a fixture in Ryder Cup lore. For golf enthusiasts who love drama and nail-biting finishes, the 1999 event is a must-study case of how momentum, nerves and a single stroke can change everything.
FAQ
Was Tiger Woods part of the 1999 Ryder Cup comeback?
Yes. Tiger won his singles match against Andrew Coltart, a win that contributed one of the vital points to the U.S. comeback.
What was the final score of the 1999 Ryder Cup?
The United States won the competition with a final score of 14.5–13.5.
Why is the 1999 Ryder Cup controversial?
The week was marked by rowdy crowds and heckling that crossed the line on multiple occasions. Several incidents involving players, family members and fans led to lasting debate about sportsmanship and crowd control at golf events.
Did Justin Leonard play a big role in the comeback?
Yes. A dramatic birdie putt on the 17th hole in his match is widely remembered as one of the turning moments on Sunday.
Is Tiger Woods going to captain the U.S. team in 2025?
As of 2024 reports, Tiger declined the opportunity to captain Team USA for 2025 and withdrew from consideration. The 2025 Ryder Cup is scheduled for Bethpage Black.
Quick Reference Table
| Item | Detail |
|---|---|
| Event | 1999 Ryder Cup at The Country Club, Brookline |
| Nickname | Battle of Brookline |
| Score after two days | Team Europe led 10–6 |
| Sunday performance | U.S. won 8.5 points in singles |
| Final score | 14.5–13.5 to the United States |
| Tiger Woods vs Coltart | Tiger defeated Coltart 3&2, match ended on the 16th hole |
| Key moment | Justin Leonard‘s dramatic putt on the 17th hole |
| Crowd issues | Heckling, hostile behavior; one player’s father walked off the course |
| Tiger’s career highlights (as listed) | 82 PGA Tour wins, 15 Major Championships, including 5 Masters and 4 PGA Championships; Hall of Fame induction in 2021 |
| 2025 Ryder Cup | Set for Bethpage Black; Tiger declined captaincy consideration in 2024 |
| Defending champions | Team Europe, winners in Rome in 2023 |
For fans who love a mix of high stakes and high emotion, Brookline 1999 remains must-see material. Whether you remember the cup live or just caught highlights later, that Sunday stands as a reminder that in match play, nothing is settled until the final putt drops.
Deeper Dive: News & Info About This Topic
HERE Resources
Keegan Bradley Named U.S. Ryder Cup Captain
Additional Resources
- Bet365 News: The Greatest Ryder Cups – 1999 The Battle of Brookline
- National Club Golfer: 1999 Ryder Cup – Colin Montgomerie & David Feherty
- Golfshake: The Battle of Brookline and The Infamous Ryder Cup
- New York Times: Brookline Ryder Cup Legend
- Wikipedia: 1999 Ryder Cup
- Golf Digest: Justin Leonard Relives 1999 Ryder Cup Putt
Author: STAFF HERE BOSTON WRITER
BOSTON STAFF WRITER The BOSTON STAFF WRITER represents the experienced team at HEREBoston.com, your go-to source for actionable local news and information in Boston, Suffolk County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as Boston Marathon, Head of the Charles Regatta, and Boston Harborfest. Our coverage extends to key organizations like the Greater Boston Chamber of Commerce and Associated Industries of Massachusetts, plus leading businesses in finance, biotech, and insurance that power the local economy such as Fidelity Investments, Biogen, and Liberty Mutual Insurance. As part of the broader HERE network, we provide comprehensive, credible insights into Massachusetts's dynamic landscape.
