Stefanos Tsitsipas beat six-time champion Roger Federer to reach the final of the ATP Finals in London.
The Greek, making his debut at the event aged just 21, won 6-3 6-4.
Swiss Federer, 38, was aiming for a record-extending seventh title but was undone by the nerveless Tsitsipas, just as he was at January's Australian Open.
Defending champion Alexander Zverev and fifth seed Dominic Thiem meet later on Saturday for the chance to play Tsitsipas in Sunday's final.
Federer was supreme in beating great rival Novak Djokovic to reach the semi-finals on Thursday but was well below his best on this occasion and was left rueing a host of missed opportunities on crucial points.
The 17-year age gap between the two players is the biggest in the history of the season-ending championships.
With the London crowd heavily in favour of Federer, Tsitsipas played the better tennis, particularly on the big points.
The Greek saved break point in the very first game before clinching Federer's opening service game minutes later with a forehand winner.
In total, Federer had six break points in the opening set but failed to take any as Tsitsipas held firm and the 20-time Grand Slam champion gifted points with errors.
Serving for the set at 5-3, Tsitsipas fought off two of those break points but saw six set points of his own come and go in a marathon game before clinching the opener on his seventh.
Federer's errors gave his opponent an further early break in the second set, only for the Swiss to finally convert a break point a game later at the 10th attempt.
But, after the crowd roared in hope of a comeback, Tsitsipas crunched another forehand winner to seal Federer's service game.
Typically, Federer had two more break points when Tsitsipas served for the match but the Greek closed out the win with some big deliveries.
Tsitsipas was aged just five when Federer won his first Wimbledon title in 2003 and said it was a "dream come true" to beat him in London.
"I grew up watching Roger here at the ATP Finals and Wimbledon and other finals," he said.
"I wished one day I could face him and today I'm here living the dream.
"I remember myself being one of the kids here watching the event and I could never picture myself here. But it can happen."
He was already the youngest player to have recorded wins against Federer, Djokovic and Rafael Nadal but this victory strengthens further his standing as one of the best young players in the game.
In his breakthrough year the world number six reached the Australia Open semi-finals and won two other titles but is now one win away from the biggest title of his career.
"Today's victory is probably one of my best moments of the season," said Tsitsipas, who 12 months ago won the Next Gen Finals - the season-ending event for the best players under 21.
"These are the moments I live for."
For Federer the tournament ends in disappointment after an underwhelming performance, where he failed to convert 11 of his 12 break points.
He lost his opening match of the round-robin stage against Dominic Thiem but after beating Matteo Berrettini and then outplaying Novak Djokovic he was tipped against to win his first title at the season-ending championships since 2011.
Against Djokovic he hit just six unforced errors in the entire match. Against Tsitsipas he made 26.
His usually impeccable forehand let him down consistently, with 17 of those errors coming off that wing, while he also missed a series of second-serve returns.
Federer fought to deuce in what proved to be the final game of the match but a wayward forehand and the shake of the head that followed summed up his performance.
"No doubt I had my chances," Federer said.
"The spells where things were not working well, they were pretty bad.
"At this level, you just can't have it happen, so that was pretty disappointing today."
The Swiss' season is now over. He will turn 39 next year but is expected to return again, looking to add to his 103 career titles - and close on Jimmy Connors all-time record of 109 - and his haul of 20 Grand Slams.