Yes in
2006 and made it to the round of 16
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Yes they have played i the 2006 world cup in Germany.
João Moutinho had played 68 times for Portugal before the 2014 FIFA World Cup.
Arturo Vidal had played 54 times for Chile before the 2014 FIFA World Cup.
James Milner had played 47 times for England before the 2014 FIFA World Cup.
Gianluigi Buffon had played 140 times for Italy before the 2014 FIFA World Cup.