Today marks the 20th anniversary of Patrick Roy’s last game with the Montreal Canadiens.

The Canadiens infamously severed ties with the future Hall of Famer following a blowout loss to the Detroit Red Wings which saw Roy give up nine goals on 26 shots before he was pulled from the game.

Roy was a member of the Colorado Avalanche just days later. He would help lead the Avalanche to its first Stanley Cup that season, their first in Colorado since relocating from Quebec City. Talk about a blow to the province of Quebec.

Jumping off of Roy’s departure from the Canadiens, here are 10 of the NHL’s most awkward breakups.

10. Kovalchuk walks away from the Devils’ millions

What would it take for you to leave $77 million on the table? For Ilya Kovalchuk all it took was comparable money in his native country of Russia.

Kovalchuk surprised the hockey world in July of 2013 when he retired just three years into a 15-year, $100-million contract he signed with the New Jersey Devils in 2010. Just days later he signed with St. Petersburg SKA of the Kontinental Hockey League.

Rumours of Kovalchuk’s interest in returning to the NHL began making the rounds shortly after he signed with SKA and still persist.

9. Blues can’t quit Craig Janney…wait, yes they can

Strap in, this one’s complicated.

Former second overall pick (1990) Petr Nedved held out from the Vancouver Canucks for most of the 1993-94 season. Nedved inked an offer sheet from the St. Louis Blues on March 5, 1994, which left an arbitrator to rule on compensation for the Canucks. Vancouver received Craig Janney and a second-round pick from Blues on March 14.

It was a ruling that did not sit well with either club. One week later the Blues reacquired Janney from the Canucks in exchange for defencemen Jeff Brown, Bret Hedican, and forward Nathan LaFayette.

Fast forward to March 5, 1995 and Janney would be on the move from St. Louis once again when he was sent to the San Jose Sharks for defenceman Jeff Norton and future considerations.

8. Canucks move on from Schneider Luongo Lack all the goalies

Roberto Luongo was the No. 1 guy in goal for the Canucks for five seasons before Cory Schneider stepped up and challenged his position on the depth chart in 2010-11.

Luongo and Schneider formed one of the best goaltending tandems in the league for two more seasons until it became apparent that it was going to be too costly to keep them both around. Luongo trade rumours dominated for some time, which only amplified the surprise factor when the club actually sent Schneider packing for New Jersey at the 2013 NHL Draft.

Then there was Luongo, his bloated contract, and Eddie Lack.

Less than a year after Schneider was traded, Luongo was on his way back to the Florida Panthers in a 2014 deadline-day deal.

Then there was Lack and Jacob Markstrom. Then there was Lack, Ryan Miller, and Markstrom. Then there was Miller and Markstrom.

Stay woke, Canucks fans.

7. St. Louis says goodbye to Lightning, Yzerman

Martin St. Louis established himself as an NHL superstar with the Tampa Bay Lightning. In 2013-14, after nearly 13 seasons with Tampa, St. Louis requested a trade to the New York Rangers.

St. Louis’ relationship with GM Steve Yzerman was seemingly damaged after he was initially excluded from Team Canada’s roster heading into the 2014 Olympic Games in Sochi. Not even a call to replace injured Lightning teammate Steven Stamkos and a subsequent gold medal could save St. Louis’ union with Tampa.

He was moved to the Rangers for Ryan Callahan in March of 2014. St. Louis retired in July of 2015.

6. Pronger puts the Oilers on his back and packs up shortly after

Even with first overall picks Taylor Hall, Ryan Nugent-Hopkins, Nail Yakupov, and Connor McDavid in the picture, perhaps no player has meant more to the Edmonton Oilers in the last decade plus than Chris Pronger.

The Hall of Famer was instrumental in a surprise run to the Stanley Cup Final in 2006, which ended in a Game 7 loss versus the Carolina Hurricanes.

Pronger requested a trade, citing personal reasons, shortly after helping inject the city of Edmonton with a healthy dose of hope. He was shipped to the Anaheim Ducks in July of 2006. He went on to win the only Stanley Cup of his career the following spring, while the Oilers have been struggling to ice a competitive hockey club ever since.

5. Jets sever ties with Kane

We now know that Evander Kane had approached the Winnipeg Jets with a trade request multiple times before his wish was finally granted.

The Jets shipped Kane, Zach Bogosian, and goaltender Jason Kasdorf to the Buffalo Sabres in exchange for Tyler Myers, Drew Stafford, Joel Armia, Brendan Lemieux and a first-round pick last February.

The move came on the heels of a falling out between Kane and his teammates that centred around the 24-year-old breaking dress code by showing up to a morning skate in a tracksuit. Teammate Dustin Byfuglien reportedly sent the winger a message by tossing his clothes in a shower stall. Kane later informed the Jets he would not be showing up for their game that night versus the Vancouver Canucks.

4. Ballard, Imlach’s antics don’t sit well with Sittler

Darryl Sittler spent nearly 12 full seasons with the Toronto Maple Leafs, sporting the captain’s “C” for six of them.

Former Maple Leafs owner Harold Ballard brought Punch Imlach back to the franchise for the 1979-80 season for a third tenure as GM. Imlach was at odds with Sittler’s agent, Alan Eagleson. Imlach angered Sittler by trading his friend Lanny McDonald to the Colorado Rockies in December of 1979 to the point that he stripped himself of the captaincy in protest.

One of the greatest Maple Leafs of all-time requested a trade and became a Philadelphia Flyer in January of 1982. He would return to the franchise in 1991, a year after Ballard passed away, as a consultant for then-GM Cliff Fletcher.

3. Heatley handcuffs Senators

Dany Heatley played some of the best hockey of his career with the Ottawa Senators, scoring 50 goals and eclipsing 100 points in back-to-back seasons from 2005-06 to 2006-07.

The former all-star requested a trade following the 2008-09 campaign, less than a year after he signed a six-year, $45-million contract with the club. Senators GM Bryan Murray had a deal in place with the Oilers, which Heatley refused to waive his no-trade clause for.

Heatley was sent to the Sharks in September of 2009 in exchange for Milan Michalek, Jonathan Cheechoo, and a second-round pick.

The Senators were forced to pay Heatley a $4-million bonus when the deal with the Oilers fell apart prior to a July 1, 2009 deadline. The two sides remained locked in a legal battle that was finally resolved over four years later in October of 2009.

2. Lindros elects to sit over spat with Flyers

For a short time, Eric Lindros was the most dominant hockey player in the world.

A string of concussions and a contract dispute with the Flyers forced Lindros to the sidelines for the entire 2000-2001 season.

No. 88 wanted out of Philadelphia, but GM Bobby Clarke was not about to make Lindros happy just for the sake of it. Clarke wanted superstar value for the former first overall pick. Negotiations with the Maple Leafs, Lindros’ preferred destination, broke down.

The Flyers finally traded Lindros in August of 2001, sending him to the New York Rangers for Kim Johnsson, Jan Hlavac, Pavel Brendl, and a draft pick.

1. Roy’s time with the Canadiens comes to an ugly conclusion

On December 2, 1995, Patrick Roy played his last game in a Montreal Canadiens uniform.

After surrendering eight goals in a game versus the Detroit Red Wings, Roy responded to mock cheers from Canadiens fans with some mockery of his own. Following the Red Wings’ ninth goal on 26 shots, coach Mario Tremblay finally pulled his superstar goaltender from the game.

Roy passed Tremblay on the bench, made his way to team president Ronald Corey, and more or less made it clear he had played his final game with the Canadiens.

Roy was suspended by the Canadiens the following day. Four days after the incident versus the Red Wings, Roy and forward Mike Keane were traded to the Colorado Avalanche for Andrei Kovalenko, Martin Rucinsky, and Jocelyn Thibault.

Roy went on to win two more Stanley Cups with the Avalanche.