Ranking the 5 greatest NHL Stanley Cup Playoff moments of all time

Bobby Orr IMAGN 041426

Ranking the 5 greatest NHL Stanley Cup Playoff moments of all time originally appeared on The Sporting News. Add The Sporting News as a Preferred Source by clicking here.

The Sporting News, established in 1886, is celebrating its 140th birthday with a year-long series honoring the greatest moments, teams and players from the last 140 years. We’ve also released SN’s entire archive for free, empowering hockey fans to download iconic print covers of Wayne Gretzky and Gordie Howe or explore endless rabbit holes to read how your favorite teams were covered in the moment.

The hockey portion of our 140 celebration continues with our picks for the top five greatest playoff moments.

5. Brett Hull’s “no goal” Cup-winning goal against Buffalo in 1999

In a moment that lives on happily in the hearts of Dallas Stars fans, and in a moment that lives in infamy for Buffalo Sabres fans, legendary sniper Brett Hull scored a controversial goal in triple-overtime in Game 6 of the Cup final in 1998-99 that pushed Dallas past Buffalo.

Depending on who you ask, Hull’s goal is either a glorious feat or an infamous example of a rule improperly applied by NHL officials.

Hull’s skate in the crease of Sabres star goalie Dominik Hasek appeared to violate a rule that invalidated a goal from counting if the skate of a player on offense entered the goal crease. However, the league ruled that Hull gained possession of the puck before pushing it past Hasek.

While Hull’s goal earned the Stars their first Cup in franchise history, it also prevented Buffalo from winning its first-ever Cup. The emotions run deep on either side of this goal, and that’s what makes this moment so memorable.

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4. Boston Bruins score three goals in less than 10 minutes, beat Maple Leafs in 2013 Game 7 showdown

This is another playoff moment that fans of the teams involved will carry with them for a lifetime, but for very different reasons.

For Boston Bruins fans, this conclusion to Boston’s 2013 Eastern Conference first-round series against the Toronto Maple Leafs is an instance of a team that didn’t give up on itself despite being down three goals in the third period.

For Maple Leafs fans, the end of this series will haunt Buds fans forever.

After Boston led the series by a 3-1 margin, the Leafs fought back to force Game 7 in Boston. And by the third period of Game 7, the Leafs led the Bruins 4-1 with slightly more than 10 minutes left in regulation time. In an all-time ‘great’ choke job, Toronto gave up three goals to send the game to overtime. From there, Bruins center Patrice Bergeron scored the game-winner and series-winner, capping off one of the greatest comebacks in league playoff history.

To this day, you can reference the game, and fans in Boston and Toronto will tell you exactly how much they hate or love the way the game unfolded.

3. Mark Messier follows through on 1994 Game 7 guarantee, leads Rangers to first Cup in 54 years

As an Original Six team, the New York Rangers had one of the longest Cup droughts in league history, as they’d last won a Cup in the 1939-40 campaign. But 54 years later, they finally ended their drought, beating the Vancouver Canucks in the 1994 Cup final.

Star center and Rangers captain Mark Messier delivered on his end in one of hockey history’s best ‘guarantees’ in Game 7 of the Rangers’ Eastern Conference final series against the New Jersey Devils.

Before Game 7 between the Blueshirts and Devils, Messier made a public guarantee of a Game 7 win. When it came time to put his money where his mouth was, Messier delivered a hat trick to win the East and set up a showdown with the Canucks, whom they also defeated in seven games. Messier is lauded for his leadership skills, but it is his ability to impose his will on games that sets him apart from 99.9 percent of NHL players.

Because of that fact, Messier occupies a prime spot in the hearts of Rangers fans.

MORE: Sporting News 140 Greatest Sports Moments: Celebrating the games we've covered since 1886

2. Gretzky’s two goals clinch the Oilers dynasty’s first cup in 1984

When he burst upon the NHL scene in 1979 with the Edmonton Oilers, Gretzky was a dynamo the likes of which the game had never seen before. Although he quickly made a major impact on the league, setting one of his slew of NHL records when he posted five assists in a single playoff game against the Montreal Canadiens in the 1980-81 playoffs, Gretzky was just getting started. In 1984, Gretzky’s dominance led the Oilers to win their first of four consecutive Cups.

With the Oilers leading their 1984 Cup final series against the powerhouse New York Islanders, Gretzky scored two first-period goals in a game that would end by a 5-2 margin to give ‘The Great One’ his first career Cup. Gretzky’s contributions started the Oilers’ dynasty and ended the Islanders’ dynasty. So Gretzky’s 1984 efforts marked a turning point in NHL history, signaling the dawn of a new era.

MORE: SN 140 Moments: No. 38 - Wayne Gretzky passes Gordie Howe to become NHL's all-time leading scorer

1. Bruins icon Bobby Orr leaps into the air after scoring OT-winner against the Blues in 1970

Whether you’re a casual hockey fan or a hard-core fan, you’ve probably seen the iconic image of Orr, a Bruins legend and one of the top-three players in NHL history, flying through the air with his arms outstretched and his body nearly parallel to the ice surface after putting the puck past St. Louis Blues icon goaltender Glenn Hall.

Orr’s heroics provided him the game-and-Cup-winning goal in the 1969-70 season, delivering the Bruins the fourth Cup in team history and their first Cup since 1940-41.

Orr’s incredible ability not only revolutionized the defenseman position, but it also serves as one of the greatest moments in the history of Boston sports. When the games mattered most, Orr rose to the occasion. And though Orr won his second and final career Cup as a member of the Bruins in 1971-72, Orr’s gravity-defying moment in 1970 forever captured the hearts of Bs fans.

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