10. 2000 New York Yankees
> Regular season record: 87-74 (0.540 win pct.)
> Regular season scoring: 871 runs scored, 814 runs allowed
> Star player: Jorge Posada
It is odd to think of the Yankees as underdogs, especially in 2000, with the team coming off their second straight title. The 2000 team had only the fifth best record in the AL, at 87-74, but still won the AL East. New York ended the regular season with a seven-game skid, but its championship pedigree kicked in once the postseason started. The Yankees defeated the A’s and Mariners in the AL playoffs, then beat their crosstown rival Mets to capture their third straight World Series.
9. 1985-86 Montreal Canadiens
> Regular season record: 40-33-7 (0.544 point pct.)
> Regular season scoring: 330 goals scored, 280 goals allowed
> Star player: Larry Robinson
Going into the 1985-1986 season, the Edmonton Oilers were heavy favorites to win their third straight Stanley Cup. All other teams, including the Montreal Canadiens, were an afterthought. The Habs finished second in their division and fifth in their conference. But many dominant regular season teams lost early in the postseason, so Montreal had a relatively easy road to the Finals. There, they met the Flames, who had shocked the Oilers in the Division Finals, and beat them in five games to hoist the Cup.
8. 1989-90 Edmonton Oilers
> Regular season record: 38-28-14 (0.563 point pct.)
> Regular season scoring: 315 goals scored, 283 goals allowed
> Star player: Mark Messier
After trading away Wayne Gretzky, the future appeared uncertain for the Edmonton Oilers. The team won the Stanley Cup in 1987-88, Gretzky’s final season with the team, then lost in the first round to Gretzky’s Kings the next year, prompting head coach Glen Sather to step down. Six teams had better odds to win the Cup going into the 1989-90 season, but the Oilers persevered to win their fifth Cup in seven seasons.
7. 1990-91 Pittsburgh Penguins
> Regular season record: 41-33-6 (0.550 point pct.)
> Regular season scoring: 343 goals scored, 308 goals allowed
> Star player: Mark Recchi
Going into the 1990-91 NHL season, just three teams had worse odds to win the Stanley Cup than the Pittsburgh Penguins. Even as late as March, the team was barely above .500 but still won a relatively weak division. This earned them favorable matchups against mediocre Devils and Capitals teams early in the postseason. The Pens knocked off the 44-24-12 Boston Bruins to make it to the Cup Finals. There, they faced a surprising upstart Minnesota North Stars team that went just 27-39-14 in the regular season, and they beat Minnesota 4-2.
6. 1994-95 Houston Rockets
> Regular season record: 47-35 (0.573 win pct.)
> Regular season scoring: 103.5 points per game scored, 101.4 points per game allowed
> Star player: Hakeem Olajuwon
After winning the NBA title the season before, the Houston Rockets seemed to be running out of gas toward the end of the 1994-1995 season. They ended their season on a three game skid to finish 47-35, earning the sixth seed in the Western Conference. But they proved their championship mettle in the playoffs, beating high-powered teams like the Jazz, Suns, and Spurs on their way to the NBA Finals. There, they met a young, talented Orlando Magic team led by Shaquille O’Neal. But the Magic were no match for the experience of Hakeem Olajuwon, Clyde Drexler, and the rest of the Rockets. Houston won its second straight title in a sweep.