Great Britain’s hopes of reaching the Davis Cup semi-finals were hanging by a thread after Jack Draper lost the opening rubber to Serbia’s Miomir Kecmanovic in Malaga.
Draper’s 7-6 (2) 7-6 (6) defeat left Cameron Norrie needing to hand Novak Djokovic just his seventh loss of the season to send the tie to a deciding doubles.
Serbia sprang a surprise by picking Kecmanovic, ranked five places above Draper at 55 in the world, ahead of their number two Laslo Djere, but the 24-year-old fully justified the decision with an impressive display.
Twenty-one-year-old Draper was unable to impose his big game on the match and came out on the wrong end of two tie-breaks in a contest lasting two hours and two minutes.
The tie did not get under way until 6.10pm, more than two hours later than billed, because of the over-running first match of the day between Italy and the Netherlands.
Around 5,000 British fans, including Dan Evans, who was forced out of the event through injury after playing the leading role in qualification, made up the majority of a virtually full crowd at the Palacio de Deportes Martin Carpena.
The International Tennis Federation’s decision to move away from the traditional home-and-away format and to a World Cup-style event has been unpopular with players and fans, but this was the sort of occasion they would have envisaged.
It was a huge moment for Draper, who only played his first match in the competition in September in Manchester and now found British hopes depending on him given the presence of Djokovic in the second rubber.
He could draw on better recent form than Kecmanovic, having reached his first ATP Tour final in Sofia earlier this month while the Serbian had lost his last four matches, and also won their only previous meeting on clay in May.
But Kecmanovic is a quality player who was ranked in the top 30 at the start of the year and, despite three aces in his first service game from Draper, it was the Serbian who was the more impressive in the early stages.
Draper had to dig deep to save two break points in a long eighth game and then found himself facing two set points at 4-5, which he again fought off in gutsy fashion.
But two double faults cost him dearly in the tie-break and left him with a lot of work to do to turn the match around.
Neither man faced a break point in the second set, but again it was Kecmanovic who looked the more convincing on serve.
After losing five points in a row from 2-0 up in the tie-break, Draper did well to level at 5-5 and then save a match point with a volley that just caught the line, but a wayward forehand gave Kecmanovic a second chance and this time the British youngster netted a return.
Nadal slumps out of Madrid Open as farewell appearance comes to a halt
Jiri Lehecka claimed a memorable win over one of tennis' greats as he downed Rafael Nadal at the Madrid Open.
Nadal's farewell appearance at the tournament he has won five times came to an end with a 7-5 6-4 defeat on Tuesday.
The 22-time grand slam champion had been hoping to tee up a quarter-final against Daniil Medvedev.
Ultimately, though, world number 31 Lehecka was the man who progressed.
Lehecka ruined the hopes of the Nadal fans packed into the stands in the Spanish capital, and took control when he reeled off 10 straight points to take the opening set.
Nadal won the Madrid Open in 2008, 2010, 2013, 2014 and 2017, and said farewell to the crowd in an on-court interview following his defeat.
Data Debrief: Nadal falls short of milestone
Nadal had been hoping to win his 60th match at the Madrid Open, while he would have reached his 100th ATP Masters 1000 quarter-final had he won. This was his first defeat to a player ranked lower than 20th in the world since he went down to Pablo Cuevas in 2016.
Lehecka, meanwhile, will make his second appearance in the last eight of a Masters 1000 event.
Auger-Aliassime gets the better of Ruud as Medvedev hits Masters 1000 milestone
Casper Ruud's hopes of building on his victory at the Barcelona Open were ended as he lost to Felix Auger-Aliassime at the Madrid Open.
Auger-Aliassime will now face top seed Jannik Sinner in the quarter-finals, after claiming a 6-4 7-5 victory over the fifth seed Ruud on Tuesday.
Ruud, runner-up at last year's French Open and a force to be reckoned with on clay, won in Barcelona earlier in April, but came unstuck against the Canadian.
It was not the only shock exit, as Alexander Zverev, the world number five, succumbed in straight sets to Francisco Cerundolo.
Earlier, Daniil Medvedev claimed his place in the quarters, in which he could face Rafael Nadal, by beating Alexander Bublik 7-6 (7-3) 6-4.
Data Debrief: Medvedev's milestone
Five of the six quarter-finals Medvedev has reached on clay have come at either ATP Masters 1000 or grand slam level.
He has now reached at least the quarter-final stage at all nine Masters events, too.
Alcaraz matches Nadal record as reigning champion scrapes into Madrid Open quarters
Jan-Lennard Struff made life difficult for Carlos Alcaraz, but the reigning Madrid Champion eventually made it through.
Alcaraz had won both of his opening games with the minimum of fuss, but he needed three sets to get beyond Struff, who won a second-set tie-break.
However, Alcaraz eventually prevailed in the decider, clinching a 6-3 6-7 (5-7) 7-6 (7-4) victory.
Alcaraz, who is in the hunt for a third straight title in Madrid, will now face seventh-seed Andrey Rublev for a place in the last four.
Data Debrief: Prodigal son matches the master
There have been plenty of comparisons between Alcaraz and his fellow Spaniard Rafael Nadal.
And with his win on Tuesday, Alcaraz matched Nadal's record for the longest winning run at the Madrid Open, at 14 matches, since the tournament began in 2002.
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