Then-Leafs general manager Cliff Fletcher shipped sniper Gary Leeman to the Flames for veteran Doug Gilmour as part of a 10-player trade-- the largest in NHL history.
Looking back, the trade proved to be a crossroads for both franchises.
Gilmour became one of the Leafs' most celebrated leaders and productive scorers. In 392 games, he amassed 131 goals and 452 points and led the once moribund franchise to back-to-back Western Conference final appearances.
Doug Gilmour amassed he amassed 131 goals and 452 points in 392 games with the Leafs. (CP Photo)
Leeman, on the other hand, scored nine goals in his two years in Calgary and the Flames haven't won a playoff series since.
So given the history, it's fitting that Gilmour's second stint with Maple Leafs begins in Calgary on Thursday.
Toronto re-acquired the popular former captain from the Montreal Canadiens for future considerations in a trade-deadline deal on Tuesday.
Gilmour played an integral role in Calgary's lone Stanley Cup championship in 1989, and is relishing the opportunity help the Leafs make a playoff push.
"It's a dream come true again,'' Gilmour said. "Hopefully I can be a small piece of this puzzle.
"This is probably my last go at (a Stanley Cup). I'm really excited about it."
At 39-years-old, Gilmour is expected to take on limited role on the Leafs' third or fourth line.
"(Leafs coach Pat Quinn) said I'd come in and play 10 to 14 minutes a game," said Gilmour. "It's a great hockey club.
"Hopefully, we can put it all together."
In addition to Gilmour, the Leafs also acquired Phil Housley at the trade deadline and Owen Nolan and Glen Wesley just days earlier. With four deals, Toronto now has 14 forwards and nine defencemen on its roster.
Which means once Housley, Tom Fitzgerald and Gary Roberts return from injuries and Darcy Tucker finishes serving his five-game suspension, ice-time will be at a premium. Competition for playing time will be fierce. Egos could be bruised and team chemistry poisoned.
"There will be nights when there are guys not playing who are used to playing," said Leafs captain Mats Sundin. "It's going to be up to us, and myself, to make sure that we stick together and win hockey games."
Winning hockey games hasn't been easy for the Leafs in recent weeks. Toronto is 2-4-1 in their last seven contests overall.
On Monday, the Leafs ended a four-game winless streak with a 3-2 victory over the Edmonton Oilers. Sundin scored the eventual game-winner with 5:48 remaining for his 1,000th career point.
With 82 points, the Leafs sit in fifth place in the Eastern Conference and appear headed for a first-round playoff matchup with the Philadelphia Flyers.
The Flames, on the other hand, will miss the playoffs for the seventh consecutive season. With 60 points, Calgary is just two just points ahead of the last-place Columbus Blue Jackets in the Western Conference.
That said, the Flames have been better of late. Before a 5-2 loss to the Edmonton Oilers on Tuesday, Calgary had won four straight and five of its last seven contests.
Pacing the Flames' attack has been Jarome Iginla, who has 15 goals in the last 16 games. And even better levels of production could be on the horizon. Flames coach Darryl Sutter is expected to reunite Iginla with old/new linemate Dean McAmmond.
McAmmond was re-acquired from the Colorado Avalanche on Tuesday and skated on a line with Iginla and centre Craig Conroy during practice on Wednesday.
That trio was one of the NHL's best last season. Iginla led the league with 52 goals and 96 points. McAmmond scored a career best of 21 goals and 51 points. Conroy also achieved career-best numbers.
"On certain lines, for whatever reasons, certain people click together and I think that's true with (Conroy) and (McAmmond)," said Iginla. "We had a lot of fun playing together last year and hopefully we will again."
"It's a good feeling coming into a situation where you had success last year and played well," said McAmmond, who was traded to Colorado in the deal that brought Chris Drury to Calgary.
"I really want to continue on what we had last year. If that's with (Conroy) and (Iginla), that would be great."
Toronto has won three straight and six of the last eight meetings with Calgary, and has taken 16 of the last 20 meetings between these two teams.
with files from Sports Network and Canadian Press