After Canada qualified for the 1986 FIFA World Cup in Mexico, it seemed to be the first of many more trips onto soccer's biggest stage.

"It felt like we'd broke the voodoo. We'd qualified for one and we're going to qualify for all the other World Cups," says forward Carl Valentine, one of the players who tried to help Canada reach the 1994 World Cup.

"But that wasn't to be."

Canada has failed to qualify eight successive times since Mexico '86 and hasn't come particularly close most of those times.

The nearest the Canadians have come to returning to the World Cup was ahead of USA '94, when one of Canada's strongest-ever squads fell penalty kicks away from a do-or-die showdown against soccer icon Diego Maradona.

Hostile environments

In late 1992 through early '93, the final round of qualifying pitted Canada against El Salvador, Honduras and perennial powerhouse Mexico, with the Canadians facing three road games in unfriendly conditions.

"Bands playing until four in the morning, cars honking, elevators that happen to stop working, they'll put you on the 13th floor with no air conditioning," says midfielder Nick Dasovic of qualifying matches in Latin America.

"All of a sudden I looked up," he recalls of the time he was stretchered off injured in El Salvador. "And there were bags upon bags of urine flying through the air."

Canadian John Catliff, left, clashes with a Mexican defender during a World Cup qualifier in Toronto in 1993. (Covershots for Canada Soccer / Flickr)

But Canada held its composure and finished second in the group — not enough to qualify for the World Cup outright, but enough to put the Canadians through to a two-game, total-goals playoff against Australia, the champion of the Oceania region.

"We felt comfortable and confident that we could win that series," says forward Alex Bunbury.

Battle in Alberta

An eventful first leg unfolded on a gusty Alberta afternoon before close to 30,000 fans at Edmonton's Commonwealth Stadium.

"We looked up and everything was red and white," Dasovic says of the crowd. "That's why we loved playing there."

“Edmonton was always great for us. We found a home there for our qualifying. They supported us really well," said Craig Forrest of the Commonwealth Stadium fans. (Canada Soccer / Flickr)

Australian goalkeeper Robert Zabica was sent off after 17 minutes, but the visitors struck first when an arching cross forced Dasovic into an awkward clearing attempt that he ended up knocking into his own goal.

"The ball came in and I went to hit it and the wind took it," remembers Dasovic. "You get over it."

But a second-half rally produced two Canadian goals in seven minutes — first from Mark Watson, then from Domenic Mobilio.

The game ended with Canada taking a narrow 2-1 lead back to Australia for the return leg.

"With the wind behind us in the second half, I thought we should've scored three or four," says goalkeeper Craig Forrest.

Still, manager Bob Lenarduzzi was optimistic.

"I felt going back to Australia we gave ourselves a good chance."

Canadian captain Colin Miller, left, shakes hands with Australian captain Graham Arnold ahead of the first leg of their sides' playoff. (Canada Soccer / Flickr)

Sydney shootout

In Sydney for the second leg, the home side came out with a first half that manager Eddie Thomson called "the best I've ever seen from an Australian team" and took a 1-0 first-half lead.

Lyndon Hooper responded for Canada before Mehmet Durakovic's looping header tied the total-goals match at 3-all with less than 15 minutes to play.

Canadian forward Alex Bunbury, left, chases down the ball during the playoff against Australia. (Canada Soccer / Flickr)

A goal-less extra time sent the teams to a penalty shootout with their World Cup fates in the balance.

"Probably the worst penalties we've ever taken," remembers Forrest.

Australian keeper Mark Schwarzer, just 20 years old and making his first international start, made two diving saves to his right — first off Bunbury and then from veteran Mike Sweeney.

"To this day I remember I thought I hit it absolutely perfect," says Bunbury of his saved penalty.

"Just goes to show what can happen."

Australia scored on all four of its penalties, knocking out the Canadians and setting up another two-game playoff with a then-to-be-decided South American country.

"Shootouts are shootouts," Lenarduzzi told the Canadian Press after the game. "It's a bit like Russian Roulette."

Missing Maradona

On the same day that Australia celebrated, Argentina was in a state of panic, having lost 2-1 to upstart Colombia.

Led by a now-fading, 33-year-old Maradona, Argentina lost again to the Colombians three weeks later, this time by a shocking 5-0 score in Buenos Aries.

The result pushed them into a regional playoff versus Australia, with the winner advancing to the '94 World Cup.

Argentina's Diego Maradona in action against Australia in the two teams' 1993 win-or-go-home two-game playoff. (Pascal Rondeau / Allsport / Getty Images)

Meanwhile, the Canadians watched and wondered what might have been.

"It'd have been an unbelievable experience," says Valentine of a Maradona matchup. "Almost like playing in a World Cup."

The result left Canada ruing its misses even more as a rusty Argentina needed a fortunate own-goal in the second half of the second leg to advance against the Australians.

"They were beatable," says Bunbury of Argentina.

At the World Cup, Maradona's Argentina proved Bunbury correct, finishing third of four teams in their group and managing to beat only World Cup debutantes Greece and Nigeria before crashing out in the second round.

Canadian players salute the fans in Edmonton after defeating Australia 2-1 in the first leg of their playoff in July 1993. (Canada Soccer / Flickr)

For many Canadians, the sting of '93 still burns.

"I don't think there's been a better pool of Canadian soccer players," says Bunbury.

While the disappointment of not repeating Canadian soccer history endures, knowing they came closer than any other Canada squad in the 25 years since remains a point of pride among the players.

"The '93 team was as good as any we've ever had," says Forrest. "If we had it now, we'd qualify quite comfortably."