Cameron Norrie ultimately suffered disappointment as his ATP finals bow ended in a three-set defeat to Casper Ruud.
The British number one was drafted in to replace Stefanos Tsitsipas after the Greek withdrew from the tournament with a right elbow injury, but could not pick up a win on debut as he was beaten 6-1 3-6 4-6.
It means Ruud will reach the semi finals in Turin if he defeats Andrey Rublev on Friday. Novak Djokovic is already through to the last four and is guaranteed to top Green Group.
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Norrie had arrived in Italy as second alternative and was not expecting to feature as an active player in the tournament. However, with both Matteo Berrettini and Tsitsipas unable to continue following their first matches it opened the door for Norrie to come in along with Jannik Sinner.
The Brit was keen to make the most of his opportunity and made an emphatic start as his depth of return lured some surprising errors off the Ruud forehand and helped him reel off five games in a row. Indeed, Norrie, who is only the fourth Briton to play singles in the event’s history, was rarely tested until he served for the set as he fended off a break point before getting the job done in just 33 minutes.
The second set was a cagier affair as Ruud showed more of the form that had seen him demolish Norrie 6-0 6-2 in the 2021 San Diego final in their only previous meeting. Both players looked strong on serve until Norrie blinked first with a pair of unforced errors off the forehand and a timid volley into the net that allowed the world number eight to snare the decisive break and go on to force a decider.
Ruud began to threaten more as he applied pressure on the Norrie serve and it paid huge dividends in game five of Set 3 when a double fault on a third break point gave the Norwegian the edge.
The momentum remained firmly with Ruud from that moment on as he once again got the better of the Brit by serving out a hard-fought battle in one-hour and 52 minutes on his fourth match point to pick up a maiden triumph at the event.
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