Andy Murray has suffered a first round defeat at the Madrid Open.
The 35-year-old former Wimbledon champion lost in straight sets to Italian Andrea Vavassori on Thursday.
Vavassori took the first set 6-2 with a convincing performance.
Murray made a bit more of a fight in the second set but again fell to defeat despite winning five of the first nine games.
The second set of the two-set match went to a tie-breaker after ending in a 6-6 draw.
The 164 ranked Italian had three match points in the tie-breaker to secure victory but squandered all three as Murray fought back to make it 6-6.
Vivassori won the eleventh game after a horrendous error from Murray to make it 7-6 and gain another match point.
Murray valiantly kept going and took it to 7-7 before falling to a 9-7 defeat in the tie-breaker and 2-0 in sets.
The loss marks Murray’s third first round defeat in a row following exits at the same stage in Miami and Monte Carlo.
The Scot could return to Wimbledon, where he was victorious in 2013 and 2016, this summer.