Where does loss to Germany rank among most painful in Canadian Olympic history?

It's a golden age for Canadian hockey fans, regardless of the men's stunning loss to Germany in Friday's semifinal at PyeongChang 2018. Canada has claimed three of the last four gold medals and, with the country's best players not permitted to leave the NHL for this year's Olympics, perhaps Canada should consider itself lucky to have advanced as far as the semifinals.

Still, losing to Germany stings. In a hockey-mad country like Canada, winning is always the expectation - particularly against an opponent with Germany's less-than-stellar hockey pedigree.

But where does Friday's loss rank among Canada's most painful defeats in recent Olympic history?

From least to most painful:

Calgary 1988

Finished fourth after final round of group play

Canada defeated the favored Soviets twice leading up to the Olympics and some believed the team was a legitimate contender for the first time in decades, but most saw this tournament for what it was: men against boys. In an era before Soviet players were permitted to join the NHL, the USSR fielded a team of world-class All-Stars like Slava Fetisov and Alexander Mogilny, plus the entire "KLM" line - Vladimir Krutov, Igor Larionov, and Sergei Makarov - while Canada sent a rag-tag collection of mostly amateurs. Perhaps it hurt a little more to finish fourth on home ice in Calgary, but it was a familiar outcome for Canadian fans, who hadn't seen a medal in hockey since 1968. We'll lump this one in with every previous defeat at the Olympics as not particularly painful.

Albertville 1992

Lost in gold-medal game to Unified Soviet Team

Canada sent a strong amateur roster to France with a legitimate chance at a medal. Featuring names like Sean Burke, tournament leading scorer Joe Juneau, and rising superstar Eric Lindros, the team advanced to the gold medal game but lost to the favored Unified Team (the former Soviet Union). The defeat hurt, but also resulted in Canada's first hockey medal since 1968 and left Canadians with real hope that their country's decades-long gold drought in hockey would soon end.

PyeongChang 2018

Lost in semifinals to Germany

There's pain in getting this close to the gold medal game and losing, and that pain is amplified when it happens against a German team that's historically been a hockey minnow, but Canadians can remind themselves that this wasn't the true Team Canada - we have NHL commissioner Gary Bettman to thank for that. Besides, was there any realistic chance of this forgettable Canadian roster beating the Russians for gold? This wound shouldn't take long to heal.

Torino 2006

Lost in quarterfinals to Russia

After finally winning gold at Salt Lake City 2002, Canada entered Torino in the unfamiliar position of looking to repeat. The tournament was a disaster for Canada, starting with a bizarre roster construction that saw Canada opt to bring defensive forwards like Kris Draper and enforcers like Todd Bertuzzi over more skilled scorers. Canada was shut out by both Finland and Switzerland in the group stage before crashing out of the tournament in the quarterfinals at the hands of Russia. Canada's seventh-place finish was its lowest in Olympic history. But it didn't take the shine off the gold won in Salt Lake City, so it was bearable.

Lillehammer 1994

Lost in gold-medal game (shootout) to Sweden

At long last, a gold-medal game without the Soviets or former Soviets. But still no gold for Canada. Sweden scored with less than two minutes to go to force overtime, then, after a scoreless period, the game was decided in a shootout. A young Peter Forsberg scored one of the greatest goals of all time on Corey Hirsch, and Paul Kariya was stonewalled on his attempt. This one really stung.

Nagano 1998

Lost in quarterfinals (shootout) to Czech Republic

In the first Olympic tournament featuring NHL players, Canada took a roster loaded with future Hall of Famers like Wayne Gretzky, Ray Bourque, and Patrick Roy. Gold was the expectation. Instead, Canada failed to win a medal after being devoured by a superhuman Dominik Hasek and the Czech Republic in the semifinals. Gretzky, infamously, wasn't selected for the shootout by head coach Marc Crawford. The image of a devastated Great One sitting on the bench will forever haunt Canadians.

(Photos courtesy: Getty Images)