# What is the most iconic NHL playoff moment of all time?

> Impossible comeback goals, controversial decisions, and moments that defined entire eras have built hockey into a sport of pure drama. Which moment do you think is the greatest?

*By YPB Team · Published May 26, 2026 · https://youpick.best/ranking/what-is-the-most-iconic-nhl-playoff-moment-of-all-time*

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## Current results (no votes yet)

1. **Bobby Orr's Flying Goal (1970)**
   Bobby Orr scored the overtime Cup winner in 1970 and was immediately tripped, creating the most iconic image in hockey history — Orr soaring through the air.
2. **Messier's Hat Trick Guarantee (1994)**
   Mark Messier publicly guaranteed a Rangers win in Game 6 of the Conference Finals — then scored three third-period goals to back it up and save their season.
3. **Mario Lemieux's Five Goals (1989)**
   Mario Lemieux scored five goals against the Flyers in a single playoff game in 1989 — a feat only one other player had managed since 1944.
4. **Ray Bourque Lifts the Cup (2001)**
   After 22 seasons without a championship, Bruins legend Ray Bourque finally lifted the Stanley Cup with Colorado — and captain Joe Sakic handed it to him first.
5. **Brett Hull's No-Goal (1999)**
   Hull's skate was visibly in the crease when he scored the Cup winner in triple overtime for Dallas — the controversy haunts Buffalo Sabres fans to this day.
6. **Patrick Kane's Cup Winner (2010)**
   Kane scored the Cup-winning overtime goal in such a blur that it took several seconds for anyone in the arena to realize the puck had gone in.
7. **Steve Yzerman's Double OT Winner (1996)**
   Yzerman's second overtime laser from the point in Game 7 of the Western Conference Semis eliminated St. Louis and became one of the great clutch moments in Wings history.
8. **Wayne Gretzky's Penalty Shot (1987)**
   Gretzky refused to take a penalty shot against Ron Hextall during the '87 Cup Finals — with good reason, as Hextall was the league's most terrifying goalie.
9. **Paul Henderson's Summit Series Goal (1972)**
   Though technically not an NHL playoff game, Henderson's winning goal in Game 8 against the Soviets is the most celebrated moment in Canadian hockey history.
10. **Theo Fleury's 1991 OT Goal**
   Fleury's overtime goal against the Kings in the 1991 Smythe Division Finals, where he skated the length of the ice in celebration in one of the NHL's most exuberant moments.
11. **Rangers End the Curse (1994)**
   The New York Rangers won the Stanley Cup in 1994, ending a 54-year championship drought in an unforgettable Game 7 against the Vancouver Canucks.

Tags: sports, hockey, nhl, all-time