[2] Winnipeg beat both Santo Domingo, Dominican Republic, and Bogotá, Colombia in 1994 to win hosting rights for the event.

[6] In 1988, a delegation from Winnipeg announced that once it got approval from the Canadian Olympic Association, the city would submit a bid to host the 1999 Pan American Games.

Canadian Bidding Committee Co-Chairman Don Mackenzie managed to convince delegates from three National Olympic Committees to change their votes before the tiebreaker round, focusing on the fact that "Santo Domingo had no place for water-skiing, but Portage la Prairie has one of the best water-skiing facilities in Canada."

The opening ceremony of the 1999 Pan American Games took place on Friday July 23, 1999, beginning at 19:30 p.m. CDT and lasted for two hours and forty-five minutes at the Winnipeg Stadium.

[15] Seven Aboriginal Canadians, who were denied entrance into the 1967 Pan American Games, also in Winnipeg, this time entered the stadium with the torch while on canoes.

Perhaps the greatest drug scandal in the sport of track and field, since Ben Johnson's disqualification at the 1988 Summer Olympics, occurred here when Javier Sotomayor the current high jump world record holder tested positive for cocaine.

A Cuban national hero, his subsequent suspension was fought from the highest levels, with Fidel Castro claiming it was an anti-Cuba conspiracy staged by the United States.

[24] Despite a second positive test for cocaine a few months later, Sotomayor eventually had his suspension reduced by a year,[25] just in time to win the silver medal at the 2000 Summer Olympics.

[26] Canada was stripped of its gold medal for inline hockey when the team's goaltender Steve Vézina tested positive for multiple banned substances.

[28] Frequent comparisons were made to the 1967 Pan Am Games, also hosted by Winnipeg, where the United States had fielded many rising stars, such as Mark Spitz.

[28] Many high-profile athletes, of all nationalities, such as U.S. champion sprinters and Brazilian football players, were in Europe during these Pan Am games, taking part in professional events.

South American nations (with the exception of Uruguay) did not send their under-23 male soccer teams after the organizing committee refused to pay appearance money to CONMEBOL.