How many Stanley Cups did Gretzky win?

Wayne Gretzky is the arguably the greatest hockey player of all-time. Gretzky, known as “The Great One”, would flourish in the Stanley Cup playoffs finishing with numerous records and reaching the Stanley Cup finals six times – five times with the Edmonton Oilers and once with the Los Angeles Kings.

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How many Stanley Cups did Gretzky win in his six trips to the finals? Wayne Gretzky won 4 Stanley Cups. He won each of those Stanley cups with the Edmonton Oilers in 1983-84, 1984-85, 1986-87, and 1987-88. As well, in two of those trips he won the Conn Smythe trophy as the Most Valuable Player. Let’s take a look at each of those series.

Stanley Cup #1 – Edmonton Oilers 1983-1984

This was the Edmonton Oilers fifth season in the NHL, and already their second trip to the Stanley Cup Finals – they lost in the finals to the New York Islanders the year before (more on that below) and now had a rematch against the Islanders dynasty, who had won 4 Stanley cups in a row.

Edmonton Oilers won Series 4-1

The Oilers would split the first two games in New York, before coming back to Edmonton to win three in a row to close out the series. Here is the breakdown of how Edmonton and Gretzky performed in the series:

Game #DateHomeScoreVisitorGoalsAssistsPointsShots
1May 10
New York Islanders0 - 1Edmonton Oilers0000
2May 12New York Islanders6 - 1Edmonton Oilers0000
3May 15Edmonton Oilers7 - 2New York Islanders0222
4May 17Edmonton Oilers7 - 2New York Islanders2022
5May 19Edmonton Oilers5 - 2 New York Islanders2136

Gretzky played better as the series went along, having his best game in the clinching series game 5 with two goals and one assist. The Conn Smythe for playoff MVP was not given to Gretzky but his close friend Mark Messier.

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Stanley Cup #2 – Edmonton Oilers 1984-85

Edmonton was the class of the NHL once again and Gretzky had managed to win this fifth straight scoring title. This all led to another Stanley Cup finals appearance – their third straight – and this time against the Philadelphia Flyers.

Edmonton won the series 4-1

Edmonton lost the first game in which coach Glen Sather was so mad he burned the tape of the game. From there the Oilers won a close game and then Gretzky almost single handedly pulled Edmonton to three consecutive wins.

Game #DateHomeScoreVisitorGoalsAssistsPointsShots
1May 21
Philadelphia Flyers4-1Edmonton Oilers0000
2May 23Philadelphia Flyers1-3Edmonton Oilers1015
3May 25Edmonton Oilers4-3Philadelphia Flyers3147
4May 28Edmonton Oilers5-3Philadelphia Flyers2025
5May 30Edmonton Oilers8-3Philadelphia Flyers1348

Gretzky would cap off a dominant regular season with his most dominate playoff appearance capturing 47 points. For all of his effort Gretzky was awarded the Conn Smythe trophy as playoff MVP.

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Stanley Cup #3 – Edmonton Oilers 1986-87

After falling out of the playoffs the previous year in an upset to their biggest rivals the Calgary Flames, the Edmonton Oilers managed to get back to the cup finals. The Oilers would find themselves in the finals once again against the Philadelphia Flyers, both of whom had the best two records in the regular season .  This rematch of the 1985 finals would be the hardest fought finals of all the Oilers appearances.

Edmonton won the Series 4-3

Game #DateHomeScoreVisitorGoalsAssistsPointsShots
1May 17
Edmonton Oilers4-2Philadelphia Flyers1125
2May 20Edmonton Oilers3-2Philadelphia Flyers1127
3May 22Philadelphia Flyers5-3Edmonton Oilers0111
4May 24Philadelphia Flyers1-4Edmonton Oilers0332
5May 26Philadelphia Flyers4-3Edmonton Oilers0114
6May 28Edmonton Oilers2-3Philadelphia Flyers01112
7May 31Edmonton Oilers3-1Philadelphia Flyers0114

Gretzky had another strong series, although the point totals were not as high as expected. This had less to do with Gretzky and more to do with Flyers goalie Ron Hextall who won the Conn Smythe despite losing, becoming only the fourth person to do so.

Stanley Cup #4 – Edmonton Oilers 1987-88

The Edmonton Oilers and Wayne Gretzky would be making their fifth Stanley Cup appearance in six years on their way to their fourth Stanley Cup. This would be the first time they would be matched up against the Boston Bruins who were led by Ray Bourque and Cam Neely. The series would not be that close as Edmonton easily won 4 games to 0. However, the most memorable event of this final was in the middle of game four with the scored tied 3-3, the lights at the Boston Gardens went out. The game was suspended at that point and the game was replayed from the start in Edmonton.

Edmonton won the Series 4-0

Game #DateHomeScoreVisitorGoalsAssistsPointsShots
1May 18
Edmonton Oilers2-1Boston Bruins1013
2May 20Edmonton Oilers4-2Boston Bruins1237
3May 22Boston Bruins3-6Edmonton Oilers0442
4 (Suspended)May 24Boston Bruins3-3Edmonton Oilers
5May 26Edmonton Oilers6-3Boston Bruins1233

Gretzky had another fantastic playoff run setting a playoff record with 31 assists in only 18 games. All of this led to Gretzky being named the Conn Smythe winner as the Most Valuable Player in the playoffs for the second time.

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Even with all of this achievement nobody knew what was going to come next, as Gretzky ultimately had played his last game for the Oilers as he was traded to the Los Angeles Kings in the offseason. This would end the Oilers dominance and also be the last time that Gretzky got to hoist the Stanley Cup, bringing his career total to 4.

RELATED: How many Stanley Cups did Mario Lemieux win? Was it more than Gretzky?

Stanley Cup Loss #1 – Edmonton Oilers 1982-83

In Gretzky’s first Stanley Cup appearance with the Edmonton Oilers he faced off against the dynasty of the New York Islanders. The Islanders had won the previous three Stanley Cups and made fairly easy work of the Oilers dispatching them 4-0.  The Oilers only managed to score 6 goals in the entire series with Gretzky collecting 4 assists.

The Islanders did a masterful job of keeping the Gretzky and the rest of the Oilers high powered offence in check, as they limited their space and kept all the shots to the outside taking away in high-danger score chances. Gretzky and the Oilers would ultimately learn from this series and use it as a springboard on their way to the their first Stanley Cup the next season.

Stanley Cup Loss #2 – 1992-93 Los Angeles Kings

Gretzky would make his last Stanley Cup appearance by leading the Los Angeles Kings to their first Stanley Cup appearance in their franchise history.  Despite winning the first game the Kings would lose the next four games to the Montreal Canadians on the way to a 4-1 series loss.

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