Matteo Berrettini defeated Andy Murray 6-4 6-4 6-7 (1-7) 6-3 to book a last-16 place at the US Open.
Murray has now failed to reach the first round at a Grand Slam for the first time since Wimbledon in 2017.
Murray struggled with his serve in the opening two sets and lost three of his five break points.
He admitted to struggling to find the rhythm to serve, which contributed largely to his loss.
"I served pretty poorly for a large part of the match, which hurt me a lot. It's always tough down one end at that time of day [because of the sun]," said three-time major champion Murray.
"From one end, it is understandable, but I just couldn't find any rhythm on serve."
"He served extremely well and got loads of free points on his serve. I didn't. That was the difference," said Murray.
British number one Cameron Norrie will be in action against Holger Rune on Saturday in the round of 32.
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