← Back to News Channel

Greatest Duels: The Most Unforgettable Sunday Singles Matches in Ryder Cup History

RyderCupPlayers.com Staff•September 26, 2025•Updated: October 5, 2026•2 min read

Three memorable Ryder Cup singles matches: Nicklaus and Jacklin in 1969, Leonard and Olazábal in 1999, and Reed and McIlroy in 2016.

The Ryder Cup's singles matches have produced moments that live far beyond the final score. These three contests show different sides of the event: a concession, a comeback and a tightly fought modern rivalry.

1969: Jack Nicklaus and Tony Jacklin at Royal Birkdale

Nicklaus conceded Jacklin's short par putt on the final green, halving their match and leaving the teams tied 16–16. It was the first drawn Ryder Cup, and the United States retained the trophy as defending champion. The official 1969 results and account record the concession after Nicklaus had holed his own return putt.

The gesture became known as “The Concession.” Its significance lay in Nicklaus removing the risk of a missed short putt for his opponent with the team result still at stake. Golf Digest's historical account describes how the act secured both the halved match and the drawn Cup.

1999: Justin Leonard and José María Olazábal at Brookline

The United States began Sunday trailing 10–6. Leonard's long birdie putt on the 17th was central to the comeback, but the celebration began before Olazábal had attempted his own birdie putt.

After Olazábal missed, Leonard was one up with one hole remaining, guaranteeing the half-point the Americans needed. Their match ultimately finished tied, and the United States won 14½–13½. The Ryder Cup's comeback history and Sky Sports' account of the controversy explain why the putt and the premature celebration remain inseparable parts of the story.

2016: Patrick Reed and Rory McIlroy at Hazeltine

Reed and McIlroy met in the opening singles match, trading birdies and animated reactions before Reed won 1 UP. The official contemporary report records the result; Sky Sports' singles review places the duel within the United States' 17–11 victory.

The match offered an example of how a single point can carry the emotion of the wider contest, even while eleven other singles matches still have to determine the team outcome.