Raonic became the fourth player to suffer 10 losses to Djokovic without once beating the Serbian star after his defeat on Rod Laver Arena.
The Canadian joined Gael Monfils, Jeremy Chardy and Andreas Seppi on Djokovic's list of opponents he has well and truly dominated on the ATP Tour.
We take a look at the four's less-than-fantastic record.
GAEL MONFILS (0-16)
The exciting Frenchman has a game to beat most players, but clearly not Djokovic. Monfils has had his chance on every surface and fallen on every occasion. He did beat Djokovic when they met at a futures tournament in Italy in 2004 but, at ATP and grand slam level, it has been one-sided. Monfils has had his moments, with only eight of the 16 ending in straight sets, but he has never been able to get over the line, beginning at the 2005 US Open and more recently at this year's ATP Cup.
JEREMY CHARDY (0-13)
Another Frenchman, Chardy has been in an entirely one-sided match-up since 2009. Incredibly, all 13 of Djokovic's wins have come in straight sets, even when Chardy has been ranked as high as 25 at Wimbledon in 2013. Djokovic has been ranked in the top four in 12 of these matches and never had any problems against Chardy, who reached the Australian Open quarter-finals in 2013.
ANDREAS SEPPI (0-12)
Seppi has come close to upsetting Djokovic previously, but this is just another match-up that suits the 16-time grand slam champion. The Italian journeyman likes to sit behind the baseline, a position on the court from which few can match it with Djokovic. Since their first meeting in 2006, Djokovic has won nine of their 12 matches in straight sets and survived a gigantic scare in another. That came at the 2012 French Open, when Seppi won the first two sets before falling to the eventual runner-up.
MILOS RAONIC (0-10)
Raonic's biggest strength – his serve – may be a huge advantage in most matches, but rarely when he is taking on arguably the best returner in the sport's history. That has proven to be the case, although four of his 10 losses to Djokovic have come on clay. Since 2013, Raonic has lost eight of the meetings in straight sets, while eight of the 26 sets between them have gone to tie-breaks, seven of those won by Djokovic. Unlike some of the others on this list, the 29-year-old Canadian may get a chance to end the unwanted record.
Edmund reached his third ATP Tour decider and first since 2018 with a 6-1 6-4 thrashing of Miomir Kecmanovic in their semi-final.
The British eighth seed needed just 71 minutes to brush past Kecmanovic, converting three of seven break points.
Awaiting Edmund in the final of the ATP 250 tournament is Seppi after the Italian veteran beat qualifier Jason Jung 6-3 6-2.
Seppi, 35, is a three-time title winner on the ATP Tour, although the last of those came in 2012.
At the Argentina Open, Norwegian eighth seed Casper Ruud overcame Juan Ignacio Londero 4-6 7-5 6-1 in their semi-final.
Ruud's win means he will become Norway's highest ranked male player ever, taking the record from his dad Christian, who reached 39th in the world in 1995.
Into his second ATP final, Ruud will face Pedro Sousa after the lucky loser's run continued.
Sousa moved through after Diego Schwartzman withdrew from their semi-final due to a leg injury.
The Argentinian had struggled late in his win over Pablo Cuevas on Friday, when he needed three hours, 41 minutes to advance.
Raonic advanced to the Australian Open quarters before falling to eventual champion Novak Djokovic last month, however, the Canadian was stunned in New York on Wednesday.
Kwon weathered 33 aces from Raonic as the South Korean prevailed after two hours, 25 minutes at the ATP 250 tournament midweek.
"I'm really happy to win a tough match against Raonic," Kwon during his on-court interview. "He played well. It was a great match."
Next up for Kwon is either eighth seed Kyle Edmund or Dominik Koepfer.
While Raonic bowed out, fellow seeds Ugo Humbert and Miomir Kecmanovic progressed from the last 16.
French fourth seed Humbert eased past Marcos Giron 6-1 6-0, sixth-seeded Serb Kecmanovic defeated Paolo Lorenzi 6-3 6-3, while Andreas Seppi saw off Steve Johnson 7-6 (7-4) 6-3.
At the Argentina Open, fourth seed Coric was sent packing by Thiago Monteiro – who won 6-4 7-6 (8-6) in Buenos Aires.
Despite letting a match point slip at 6-5 in the second-set tie-break, Monteiro moved through to his first ATP Tour-level quarter-final since 2018.
Pedro Sousa awaits after the lucky loser accounted for Jozef Kovalik 7-6 (7-3) 7-6 (7-5) on the clay courts.
Dusan Lajovic – the third seed – outlasted qualifier Pedro Martinez 7-6 (8-6) 7-6 (8-6) to set up a quarter-final with eighth seed Casper Ruud, who dismantled Roberto Carballes Baena 6-1 6-0.
Briton Edmund – contesting his first ATP Tour final since 2018 – claimed a 7-5 6-1 victory in New York.
The eighth-seeded Edmund prevailed over Italian opponent Seppi after one hour, 21 minutes for his second ATP crown.
Edmund, who reached the 2018 Australian Open semi-finals, used his serve to see off Seppi on the American hard courts at the 250 tournament.
The South Africa-born Edmund won 31 of his 33 first serve points and did not face a break point throughout the match.
Edmund broke three times en route to his first trophy since winning the 2018 European Open in Belgium.
Schwartzman, the top seed in Buenos Aires, needed three hours, 41 minutes to edge Pablo Cuevas 5-7 7-6 (13-11) 7-5 in an epic battle at the ATP 250 tournament.
The Argentinian, last year's runner-up, saved four match points in the second set before overcoming Cuevas.
Schwartzman managed two breaks of serve in the deciding set, including the decisive one in the 12th game.
Awaiting him in the semi-finals is Pedro Sousa, the lucky loser continuing his run with a 7-6 (7-5) 6-4 victory over Thiago Monteiro.
Casper Ruud will face Juan Ignacio Londero in the other semi-final after their respective wins over Dusan Lajovic and Guido Pella.
At the New York Open, Opelka's title defence came to an end with a 5-7 6-4 6-4 loss to qualifier Jason Jung.
Opelka served 24 aces, but the 2019 champion was broken twice to fall to defeat in one hour, 52 minutes.
Jung will meet Andreas Seppi in a semi-final after the Italian veteran got past Jordan Thompson 6-7 (2-7) 6-4 6-1.
Kyle Edmund advanced thanks to a 3-6 6-2 7-6 (7-5) win against Kwon Soon-woo, while Miomir Kecmanovic beat Ugo Humbert 3-6 6-2 6-4.
