Golfers Who Lost the Most Ryder Cup Singles Matches

In the history of the Ryder Cup, there are (so far) seven golfers who've each lost at least six singles matches. And the recordholder? That is Christy O'Connor, who, over the course of his long Ryder Cup career, lost 10 singles matches.

Only one American golfer is among those who've lost six or more singles matches, but it's a big one: Phil Mickelson. (Related: Who won the most Ryder Cup singles matches?)

The List: Most Losses in Ryder Cup Singles

For each golfer here, we list all of his singles losses, along with his overall record in singles.

Christy O'Connor, 10 singles losses

Christy O'Connor holds the overall record for most losses in singles match play in the Ryder Cup. O'Connor played 14 singles matches for the Great Britain/Great Britain and Ireland teams, and lost 10 of them. He first played in the 1955 Ryder Cup, and last in the 1973 Ryder Cup. His overall singles record was 2-10-2 (two wins, 10 losses, two halves). The list of O'Connor's singles losses:

1955: lost to Tommy Bolt, 4 and 2
1959: lost to Art Wall, 7 and 6
1961: lost to Dow Finsterwald, 2 and 1
1963: lost to Gene Littler, 1-down
1963: lost to Billy Maxwell, 2 and 1
1965: lost to Tony Lema, 6 and 5
1967: lost to Bobby Nichols, 3 and 2
1969: lost to Gene Littler, 2 and 1
1971: lost to Gardner Dickinson, 5 and 4
1973: lost to J.C. Snead, 1-down

His two wins came against Dow Finsterwald and Frank Beard.

Tony Jacklin, 8 singles losses

Tony Jacklin is runner-up with eight losses (out of 11 singles matches). From 1967 through 1979, Jacklin compiled an overall singles record of 2-8-1.

1967: lost to Arnold Palmer, 3 and 2
1967: lost to Gardner Dickinson, 3 and 2
1971: lost to Lee Trevino, 1-down
1971: lost to J.C. Snead, 1-down
1973: lost to Billy Casper, 2 and 1
1975: lost to Bob Murphy, 2 and 1
1975: lost to Raymond Floyd, 1-down
1979: lost to Tom Kite, 1-down

His victories were over Jack Nicklaus and Tommy Aaron. Jacklin's one draw was also against Nicklaus, and in the same tournament: the 1969 Ryder Cup, which famously ended with Nicklaus' concession of Jacklin's short putt, producing a tie in the overall score.

Lee Westwood, 7 singles losses

Westwood played 11 singles matches in Ryder Cups from 1997 through 2021. His overall record was 4-7-0.

1997: lost to Jeff Maggert, 3 and 2
1999: lost to Tom Lehman, 3 and 2
2002: lost to Scott Verplank, 2 and 1
2008: lost to Ben Curtis, 2 and 1
2010: lost to Steve Stricker, 2 and 1
2014: lost to Jimmy Walker, 3 and 2
2016: lost to Ryan Moore, 1-down

His victories were against Kenny Perry, Chris DiMarco, Matt Kuchar and Harris English.

Phil Mickelson, 6 singles losses

On the American side, the record for most singles defeats is six, and Mickelson is that recordholder. Mickelson first played in the 1995 Ryder Cup and last in the 2018 Ryder Cup. His overall singles record is 5-6-1.

2002: lost to Phillip Price, 3 and 2
2004: lost to Sergio Garcia, 3 and 2
2006: lost to Jose Maria Olazabal, 2 and 1
2008: lost to Justin Rose, 3 and 2
2012: lost to Justin Rose, 1-down
2018: lost to Francesco Molinari, 4 and 2

Mickelson's five wins were against Per-Ulrik Johansson, Darren Clarke, Jarmo Sandelin, Peter Hanson and Stephen Gallacher.

Neil Coles, 6 singles losses

Neil Coles played 15 singles matches from 1961 through 1977, with an overall record of 5-6-4.

1963: lost to Dave Ragan, 2 and 1
1965: lost to Dave Marr, 2-down
1969: lost to Dan Sikes, 4 and 3
1971: lost to Jack Nicklaus, 5 and 3
1973: lost to Lee Trevino, 6 and 5
1977: lost to Lou Graham, 5 and 3

For his wins, Coles defeated Dow Finsterwald, Billy Casper, Doug Sanders (twice) and Tommy Aaron.

Harry Weetman, 6 singles losses

From 1951 through 1963, Harry Weetman played eight singles matches and posted a record of 2-6-0.

1951: lost to Lloyd Mangrum, 6 and 5
1955: lost to Doug Ford, 3 and 2
1959: lost to Bob Rosburg, 6 and 5
1961: lost to Doug Ford, 1-down
1961: lost to Art Wall, 1-down
1963: lost to Julius Boros, 2 and 1

Weetman's wins were against Sam Snead and Julius Boros. In the 1953 Ryder Cup, Weetman was 4-down to Snead with six holes to play, then won five holes in a row to take the match.

Ian Woosnam, 6 singles losses

And the worst singles record in Ryder Cup history — yes, worse even than Christy O'Connor's record — belongs to Hall of Famer Ian Woosnam. From 1983 to 1997, Woosy played eight singles matches ... and didn't win any of them. His record was 0-6-2.

1983: lost to Craig Stadler, 3 and 2
1985: lost to Craig Stadler, 2 and 1
1987: lost to Andy Bean, 1-down
1989: lost to Curtis Strange, 2-down
1991: lost to Chip Beck, 3 and 1
1997: lost to Fred Couples, 8 and 7

That 8-and-7 loss to Couples in the 1997 Ryder Cup doesn't just share the tournament record for worst defeat in an 18-hole singles match, but in any 18-hole match in the Ryder Cup. All Woosnam could manage in eight singles matches were two draws, and they were both, also, against Couples.

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