Wayne Gretzky won four Stanley Cups in his career, all with the Edmonton Oilers in the 1980s. He only played in a single Stanley Cup Final outside of Edmonton in his career. That was, of course, with the Los Angeles Kings in 1993, when they lost to the Montreal Canadiens. No team was built for him like the Oilers were.
On this day in 1993, the Canadiens defeated the Kings to win their 24th Stanley Cup #Hockey365 #GoHabsGo pic.twitter.com/JsjTbjgDmm
— Mike Commito (@mikecommito) June 9, 2021
The biggest question was, were the Oilers built to be able to withstand losing the greatest player in franchise, if not league, history? They were about to find out following owner Peter Pocklington’s sale, aka trade, of Gretzky to LA. Now, a team built with Gretzky as its cornerstone had to carry on without Gretzky. The leader now is Mark Messier. It’s the St. Albert kid’s team, and he, along with the players who have survived Pocklington’s trades, have to drive for number five.
Previous Lookbacks have detailed how the Oilers had to learn to win with Gretzky. This one will detail 1988–89 and 1989–90, and them learning to win without him.
One thing that is often said about the Oilers of the 1980s is that the guys on the team were tight-knit. There wasn’t any drama in the locker room, there was an expectation to show up and do your job. Everybody had each other’s back, they won and lost together, and the team culture flourished.
The Oilers were generally considered Canada’s worst prom band of the early 80s – hang on, being told they were actually the best hockey team in the world. Thank god. pic.twitter.com/pDesWm5k9Q
— Super 70s Sports (@Super70sSports) October 10, 2020
When Gretzky, during the press conference for his trade, proclaimed “I promised Mess I wouldn’t do this,” he almost certainly meant it. There was a sense of kinship, that would be hard to leave behind especially right after four Cups in five years. But the even bigger question would be, how would the players handle the news?
In the immediate aftermath, the answer was mixed. A lot of players, like current Sportsnet Analyst Craig Simpson, were at a complete loss for any reaction. Some others, like future Hall of Famer Kevin Lowe, allowed themselves to feel hurt, but ultimately committed right away to forging on without Gretzky.
Naturally, the most affected people in the Oilers organization were Head Coach Glen Sather, and budding superstar Messier. It crushed both of them the deepest, and with them being arguably the closest to Gretzky, you could see why. Yet, at the same time, they also had to lead the way forward. They had to help the franchise the most in carrying on, despite the deep cuts of the move.
Nevertheless, it was time to begin a new season. And by the letter of the book, the Oilers were two-time-defending champs, for the second time in the decade. However, once the puck dropped on their 10th-anniversary 1988–89 season, it was clear there was a lot of adjustments that the team needed to make.
The Oilers played 11 games in October 1988 to open the season, and they did win the first two. They opened with a 5–1 win over the New York Islanders, and a 5–4 win over the Winnipeg Jets. The rest of the month, though, saw the team go 3–4–2, to close October just a game above .500.
The scoring prowess of the Oilers was noticeably more mercurial without No. 99. In the games they lost or tied in, only once did they score more than three goals. Conversely, in all the games they won, only once did they score less than five goals.
There would be a bit of a reprieve from the struggles in November and December for the Oilers, mercifully. From the end of October through to the Christmas break, the Oilers posted a 15–9–2 result, boosting their season record to 20–13–4. Not otherworldly dominant, but still proving they were a tough out.
After the Christmas break, however, the Oilers could not maintain the same consistency. The 1989 portion of the season calendar was very scattered and all-over-the-place. They could only manage to go 18–21–4 over that span, to finish the season 38–34–8, with their lowest point total in the standings since 1980–81.
Carson scores in the 1989 #NHL All-Star game in Edmonton #LetsGoOilers pic.twitter.com/YOGUuM9DQB
— Vintage Oilers (@VintageOilers) July 21, 2025
It ended up being the same when the playoffs came around, as they faced none other than Gretzky’s Kings in Round 1. The Oilers, to their credit, took a 3–1 series lead. But then they lost their form, and the next three games, as L.A. outscored Edmonton 16–6 in Games 5–7 to complete the comeback.
Fortunately for Oilers fans, at least, the Kings made a deal with the demons for that comeback. Some say they are still paying their dues to this day. Nobody is yet sure if four consecutive first-round eliminations is the full extent of recent debt repayment.
The Oilers, now aware completely of just how limited their chances were getting to win again, would try to start fresh in 1989–90. Same team, more or less. Same mentality of “we can win without Gretzky.” It would be far easier said than done however.
Grant Fuhr, their legendary goaltender, had to undergo an appendectomy during training camp, leaving it up to backup Bill Ranford to carry the goaltending weight. Then, Gretzky trade chip Jimmy Carson left the team only a handful of games into the season. A trade request had been put in, and he would be dealt in November 1989. And the cherry on top? Gretzky overtaking Gordie Howe as the NHL’s all-time points leader. On Coliseum ice.
So far, not so good. Remember how the 2023–24 Oilers were 5–12-1 through 18 games to start the year? The 1989–90 Oilers pioneered that sort of futile beginning. 5–8–4 was what they finished with after 17 games.
Thankfully, the Oilers would rebound from that substandard start. Messier especially was a driving force behind the Oilers staying competitive, with stalwarts Lowe, and Jari Kurri, joining Messier as All-Stars that year. And despite the several injuries Fuhr would suffer throughout the season, Ranford emerged as a capable starter in his absence.
Bill Ranford Edmonton Oilers Pro Set Card @EdmontonOilers #LetsGoOilers #NHL pic.twitter.com/6IE3Ai3NqB
— NHL Hockey Cards (@NHLHockeyCards) May 24, 2024
The Oilers would finish 38–28–14, 2nd in the Smythe Division on the season. Curiously, while the “gritty” label is more commonly applied to the Oilers of later in the decade and into the 2000s, this squad began that reputation. They finished the season averaging 25.6 PIM per game, among the highest teams in that category.
The Oilers were up three games to one on Los Angeles in 1989, only to fall apart the last three games. In the 1990 Stanley Cup Playoffs, they were down three games to one to Winnipeg, but had home ice for two of the final three games of the series. The whole moral of the story? You have to lose to know how to win.
All the Oilers needed was to win one in Winnipeg, that being Game 6. They first took care of a home Game 5 to make that a reality, then indeed stole Game 6 on the road. Those two were tight 4–3 contests that Edmonton had to grind out. Grind them out they did, before finishing things off with a 4–1 Game 7 victory.
The Kings were next. But this year, the Oilers not only had momentum, but a hunger to not let Gretzky have the last laugh again. They swept Los Angeles, this beginning a streak of playoff series wins over L.A. that continues to this day.
Mark Messier during the 1989-90 season:
— Big Head Hockey (@BigHeadHcky) July 8, 2023
79 Games Played
— 45 Goals
— 129 Points
— 6 Shot-Handed Goals
— 211 Shots
— Won the Ted Lindsay
— Won the Hart
— Swept Gretzky in the 2nd Round of the Playoffs
— Won the Stanley Cup
The 80's Oilers weren't just Gretzky pic.twitter.com/hIvRYp53l7
The rest of the 1990 story is history. Timely saves from Ranford, clutch scoring throughout the lineup including Petr Klima’s famous 3OT winner in Game 1 of the Cup Final. And all the momentum in the world on their side. It ended with a Game 5 clincher on the Boston Garden ice in late-May 1990.
Here's Petr's triple-OT goal vs. Boston that helped the #Oilers capture the 1990 Stanley Cup. pic.twitter.com/bcZ2qS8YT1
— Edmonton Oilers (@EdmontonOilers) May 4, 2023
The job was complete. The Oilers had, indeed, proven they could win without Gretzky. The pieces left from the dynasty days carried the dynasty forth, with the perfect complement of players stemming from a Gretzky trade tree that, all told, spanned an incredible 34 years before culminating. This observer, however, is not Steve Dangle and isn’t good at explaining trade trees.So instead, have this shining orange-and-blue memory.
OTD 1990
— Vintage Oilers (@VintageOilers) May 24, 2023
Game 5 Stanley Cup Final #LetsGoOilers #NHLBruins
We win our 5th Cup in 7 years.
Final major pro sports title won in the Boston Garden pic.twitter.com/cIqFLNUaaI
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