Kyle Edmund won a physical battle against Andy Murray to reach the Battle of the Brits semi-finals.
Murray, playing only his second match since November, lost 6-7 (2-7) 7-6 (7-5) 10-5 and must now beat James Ward on Thursday to advance.
The encounter was billed as good gauge of where Murray is after a pelvic injury and there were some positives.
The six-day charity event, organised by Murray’s brother Jamie, is at the National Tennis Centre in Roehampton.
Liam Broady, whom Murray beat in his opener on Tuesday, was eliminated with a 6-4 6-1 defeat by Ward in the other match in the Tim Henman Group earlier in the day.
In the Greg Rusedski Group, Cameron Norrie survived a scare against world number 393 Ryan Peniston, coming from behind to win 3-6 6-1 10-4.
Peniston, 24, was a replacement in the draw for 18-year-old Jack Draper, who pulled out with an abdominal injury.
More to follow.