Despite his disappointments in the majors, Montgomerie is heralded as one of the greatest Ryder Cup players of all time. To date he has been a member of the European team on eight occasions, and has never lost in a singles match. He holds a win-lose-draw record of 20–9–7, thus giving him a total points scored tally of 23.5, only 2 points behind the all-time record held by Sergio García. He has played pivotal roles in several of the matches. He halved the last hole with Scott Hoch to obtain the half-point that won Europe the cup in 1997, and sank the winning putt, in what is considered to be his finest hour in the 2004 staging of the event.