This year’s World Series will feature underdog vs. underdog, “David vs. David”. It seems to me this rarely happens in the championship of the four major sports. The 1997 World Series had wild card, 92 game winner Florida beating Cleveland, who won just 86 games that year. In 2006 the Cardinals won the World Series after winning just 83 games - they defeated the Tigers who were the wild card, but who won 95 games, fourth best in baseball - so I’m not sure if that qualifies.
I can’t think of any Super Bowls where both participants were surprises. And I don’t know enough about the NHL and NBA to come up with examples. But there must be some more.
The '95 World Series pitted two wild card teams against each other.
The 2006 NBA finals had the 2nd seeded Heat vs. the 4th seeded Mavericks, and the following season saw third-seeded San Antonio beat 2nd seeded Cleveland.
Super Bowl XXXV maybe? The Giants were 7-4 before running off 5 straight to end the season after posting a 7-9 record the previous year. The Ravens had one of the greatest D’s to ever take a football field but virtually no offense to speak of. Their QB’s were Trent Dilfer and Tony Banks. It was a down year in NFL overall.
The 1991 Stanley Cup Finals featured the Pittsburgh Penguins, who had the seventh best record in the NHL (of 21) and had missed the playoffs the previous year, against the Minnesota North Stars, who were sixteenth overall, and hadn’t won a best of seven playoff series since the 1984 Norris Final.
Both teams were looking for their first ever Stanley Cup win, which is more common now–it happened again in 1996, 1999 and 2007.
No. The 1995 World Series did not pit two wild card underdogs against each other. The American League Champion Cleveland Indians won the AL Central by 30 games. (Read that again). Their record was 100-44, a winning percentage of .694, making it one of the highest of all-time. Projected over the normal 162 game season that comes to 112 wins, which would’ve set the AL record at the time. Their opponent in the Series, the Atlanta Braves, won the NL East by 21 games, so they were an “overdog” too.