Raymond van Barneveld's William Hill World Darts Championship farewell ended in heartbreak with a shock first round exit, while Rob Cross also crashed out at Alexandra Palace on Saturday.
Van Barneveld's first round meeting with American Darin Young proved to be the legendary Dutch star's final professional match as he suffered a 3-1 loss in a nightmare end to his glittering career.
The five-time World Champion had received a hero's reception from the crowd as he made his way on to the sport's most famous stage but the night was to end with a cruel defeat.
"The demons won again - I never felt comfortable in the whole match," admitted van Barneveld, who announced his retirement more than 12 months ago.
"Darin played really well but I could not find anything and I am really disappointed.
"I had practised well and done everything I could to prepare but I didn't play anything like that on stage. I will never forget or forgive myself for this performance - it has been a nightmare end to a nightmare year."
Young took the first set 3-1 to pile the pressure on Van Barneveld, who battled back by taking the second set 3-0 but lost the crucial fifth leg in set three to leave himself facing defeat.
The American ace landed another blow with a 160 checkout on the way to taking the first two legs in the fourth set before Van Barneveld forced a decider - only to miss two darts to take the tie to fifth set, which his opponent punished to inflict a devastating loss.
World number two Cross was also left stunned, losing his opener in straight sets to Kim Huybrechts - who moved into round three, having seen off Geert Nentjes on Friday.
Huybrechts produced checkouts of 116 and 152 in a dominant display over the 2018 World Champion, who looked out-of-sorts throughout the encounter.
"I feel stunned - I can't really believe it," admitted the Belgian ace.
"Rob Cross did not turn up at all and I know that but I took my chances and I won. I'm very pleased to win.
"I was strong in my mind against one of the best players in the world and I'm proud of how I fought for that victory."
Luke Humphries joined Huybrechts in the third round after winning an Ally Pally classic against Jermaine Wattimena in a dramatic duel that went down to sudden-death shootout.
After seeing off Devon Petersen on Friday night, Humphries completed a memorable 24 hours with another impressive display.
Wattimena won the first set without dropping a leg and took the first leg in set two but Humphries stormed back by claiming the next three legs in just 35 darts to level up the tie.
The following two sets were shared before the final set reached a tiebreak, in which Wattimena looked to have taken pole position when he punished Humphries for a missed matched dart.
The recently-crowned PDC Unicorn World Youth Champion hit back from 5-4 down, taking out 96 before landing tops to seal glory.
"That was the most thrilling game I've ever played in," said Humphries.
"I'd love to say I stayed calm and composed but I didn't feel that way up on the stage. I do think I found the right things at the right time.
"I'm over the moon to have won that match and I showed a lot of bottle - that's what you need to win titles like this.
"I love playing here. I love the feeling I get when I am playing on the Ally Pally stage and that is the best game I've ever been part of."
Zoran Lerchbacher also upset the odds to win despite missing several match darts against Jamie Hughes.
After the first four sets were shared, Lerchbacher took a two-leg lead in the decider but squandered eight darts to seal the match, allowing Hughes to force a sudden-death shoot-out which the Austrian won on double eight.
Mark McGeeney enjoyed a debut victory as he fended off the challenge of Canada's Matt Campbell to progress to round two.
Former Lakeside Championship finalist McGeeney won each of the first two sets 3-1 before a stunning 147 finish helped Campbell halve the match deficit.
The fourth set went down to a deciding leg, which saw McGeeney wrap up the win by landing tops.
Luke Woodhouse produced an assured performance to earn a comfortable World Championship debut victory over veteran ace Paul Lim.
65-year-old Lim checked out 160 in the first leg but that was to be as good as it got for the legendary Singapore star as Woodhouse finished 81, 109 and 87 to to take the opening set.
Emerging star Woodhouse also won the following two sets 3-1 to set up a second round meeting with last year's runner-up Michael Smith.
Darius Labanauskas breezed to a straight sets victory over Matthew Edgar, who failed to recover from losing the first seven legs.
The Lithuanian talent hit three 180s in a dominant display to defeat Edgar in the opening round for the second successive year.
Japan's Yuki Yamada claimed a debut win over Ryan Meikle, who was also appearing at Alexandra Palace for the first time.
Meikle took the first set in a decider but Yamada won the crucial fifth legs in sets two and three before clinching the fourth set 3-1 to earn a notable victory.
The William Hill World Championship continues on Sunday with two sessions of first and second round ties, as last year's runner-up Smith and Lakeside Women's Champion Mikuru Suzuki join the action.
Day Three will be broadcast live on the Sky Sports Darts channel and through NOW TV in the UK, on PDCTV-HD for Rest of the World Subscribers and through the PDC's worldwide broadcast partners including DAZN and RTL7.
William Hill World Darts Championship
Saturday December 14
Afternoon Session
3x First Round, 1x Second Round
Darius Labanauskas 3-0 Matthew Edgar (First Round)
Yuki Yamada 3-1 Ryan Meikle (First Round)
Luke Woodhouse 3-0 Paul Lim (First Round)
Luke Humphries 3-2 Jermaine Wattimena (Second Round)
Evening Session
3x First Round, 1x Second Round
Mark McGeeney 3-1 Matt Campbell (First Round)
Zoran Lerchbacher 3-2 Jamie Hughes (First Round)
Darin Young 3-1 Raymond van Barneveld (First Round)
Kim Huybrechts 3-0 Rob Cross (Second Round)
Sunday December 15
Afternoon Session (1230 GMT)
3x First Round, 1x Second Round
Kyle Anderson v Xiaochen Zong (First Round)
Ross Smith v Ciaran Teehan (First Round)
Brendan Dolan v Nitin Kumar (First Round)
Ian White v Darius Labanauskas (Second Round)
Evening Session (1900 GMT)
3x First Round, 1x Second Round
Arron Monk v Jose Justicia (First Round)
Andy Boulton v Danny Baggish (First Round)
James Richardson v Mikuru Suzuki (First Round)
Michael Smith v Luke Woodhouse (Second Round)