World championship leader Max Verstappen and Red Bull teammate Sergio Perez both failed on Saturday to make it into final qualifying for the Singapore Grand Prix.
Verstappen, who has won the last 10 races in a row, finished 11th fastest in Q2 and was eliminated along with Perez, who was 13th.
Verstappen is chasing a third world title and has a massive 145-point lead over Perez.
But the Dutchman has never triumphed under the lights in Singapore and faces an almost impossible task to end the drought after a torrid weekend when the Red Bulls were well off the pace.
Perez won in Singapore last year from second on the grid, but will make his 250th grand prix start in Sunday's night race from the back half of the grid.
Red Bull have won all 14 races so far this season but Singapore's Marina Bay street circuit is shaping up as the biggest challenge to the team's unprecedented quest to win all 22 races.
Verstappen has won 12 of the 14 races this season with Perez the only other driver to take the chequered flag.
Pierre Gasly, Alex Albon and Yuki Tsunoda were also eliminated in Q2.
Earlier Q1 was brought to a premature halt by a red flag after Lance Stroll crashed his Aston Martin spectacularly entering the pit straight at the end of a hot lap.
A huge impact into the wall sent his car spinning across the track with wheels and bodywork flying.
Lando Norris was close behind and did well to avoid the wreckage in his McLaren.
The crash eliminated Stroll, who remarkably managed to walk away unaided. Valtteri Bottas, Oscar Piastri, Logan Sargeant and Zhou Guanyu also failed to make it into Q2.