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Wawrinka, the beaten finalist at Roland Garros, Paris,lost to Spain’s Feliciano Lopez 6-7, 5-7, while Raonic was beaten by another Australian Thanasi Kokkinakis 6-7, 6-7.
The defeat was Murray’s first at the tournament since 2014 and ended his 14-match winning streak on grass, stretching back to 2015.
“It’s a big blow, for sure. It has happened in the past where guys haven’t done well here and gone on to do well at Wimbledon,” Murray said.
“There is no guarantee that I won’t do well at Wimbledon, but it certainly would have helped to have had more matches,” he added.
“He played better than me. I didn’t create loads of chances. I didn’t return particularly well. He served big. He served well.”