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Westwood has been paired with Martin Kaymer against Phil Mickelson and Dustin Johnson in the first fourball.
BBC: Ryder Cup 2010: Westwood aims to lead Europe by example
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The Swede, along with Miguel-Angel Jimenez and Edoardo and Francesco Molinari, have been left out of the opening day's fourball action.
BBC: Ryder Cup 2010: Westwood aims to lead Europe by example
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And the nostalgic love-in continued for the duration of his entertaining fourball duel with partner Fred Couples against Nick Faldo and Brad Bryant.
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The event continues with five more fourball matches on Friday, followed by four greensomes and four foursomes on Saturday and 10 singles matches on Sunday.
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For instance, putting Laura Davies and Spanish rookie Paula Marti out top in both matches meant that they hardly had time to down a drink between the morning foursomes and afternoon fourball matches.
BBC: Plenty to smile about
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"When you play at the weekend with your friends in a fourball, no cards are required to be returned, " said Richard Muckart, chairman of the Council of National Golf Unions, or CONGU, which runs the program.
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The three-day matchplay event at Rich Harvest Farms near Chicago will begin with four fourball matches followed by four foursomes matches on Friday, with the same pattern on Saturday and 12 singles matches to conclude on Sunday.
BBC: Davies craves Cup success in US
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In the pro-am format, Montgomerie is playing with his brother Douglas and Ryder Cup hero Graeme McDowell, while Italian brothers Edoardo and Francesco Molinari play in the same fourball alongside amateur partner Gianfranco Zola, the former West Ham manager and Chelsea striker.
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