Cameron Norrie missed out on one of the biggest scalps of his career at Queen’s Club after going down in three sets to last year’s Wimbledon runner-up Kevin Anderson.
The British number two looked on course to kick off his grass-court campaign in style at the Fever-Tree Championships after taking the first set.
But Anderson, the world number eight, levelled the first-round match on the tie-break and a solitary break of the Norrie serve in the decider gave him a 4-6 7-6 (5) 6-4 victory.
Big-serving South African Anderson was making his comeback from an elbow injury which forced him to miss the entire clay-court season.
The ring-rust was evident as Norrie secured a break of the 33-year-old’s serve in a first game lasting eight minutes.
Norrie was hardly threatened on his serve, wrapping up the first set with a hold to love.
However, the 23-year-old had to save break points in the fourth and sixth games of the second set, while the Anderson serve was also ominously beginning to click into gear.
Norrie dug deep to hold for 6-6 and force the tie-break, only for Anderson to pinch it to level the match.
Norrie fended off one break point in the fifth game of the decider but then put a forehand long to give Anderson what turned out to be the crucial advantage.
James Ward, the British number four, also fell by the wayside, beaten by Gilles Simon of France.
Ward took the first set against the world number 38 and, having dropped the second, led 4-2 in the decider.
However, the 32-year-old, ranked 212 in the world, lost a tense final-set tie-break as Simon sealed a 3-6 6-3 7-6 (2) victory.
British number three Dan Evans faces Stan Wawrinka at lunchtime on Tuesday buoyed by some fine recent form.
The 29-year-old arrives in west London having landed back-to-back Challenger titles on the grass of Surbiton and Nottingham.
He said: “It was obviously two good weeks. I’m happy with the way I was playing. It was the perfect two tournaments for me to start the grass-court season, really.
“Even if I didn’t win, it would have been great preparation for this tournament. I’m happy with how they went, obviously, and hopefully I’ll play well tomorrow against Stan.”
Evans also confirmed he would jump at the chance to play doubles with Andy Murray at Wimbledon if the two-time champion asked.
Elsewhere at Queen’s there were wins for reigning champion Marin Cilic and fourth seed Daniil Medvedev.
British number one Kyle Edmund takes on top seed Stefanos Tsitsipas of Greece on Tuesday afternoon.