After losing to Holger Rune of Denmark in the quarterfinals of the Stockholm Open, Cameron Norrie’s chances of making it to the ATP Tour Finals were dashed.
To qualify for the season-ending event in Italy in November, the British number one, now ranked 14th in the world, has to move up to the top seven.
He won the first set, but Rune, 19, came back to win it 6-7, 6-3, 6-3.
Felix Auger-Aliassime of Canada defeated Britain’s Dan Evans in the quarterfinals of the European Open as well.
Teenager Rune will face Australian Alex de Minaur in the semifinals after defeating Norrie.
Following his withdrawal from events in South Korea and Japan last month, Norrie is already playing catch-up in his attempt to make it to the ATP Tour Finals.
Norrie overcame dropping a break in the first set against Rune to win it on a tie-break after overcoming Aslan Karatsev in the round of 16.
To earn a spot in the last four, the youngster broke serve twice in the second set and once more in the eighth game of the decider.
Meanwhile, Evans won the first set of his match against Auger-Aliassime in Antwerp, Belgium, before winning 4-6 7-6 (7-4) 6-2.
The Frenchman Richard Gasquet will now face the Canadian in the semifinal.