| Question | Team |
|---|
| This team has not had a winning season since 1997 | |
| After winng the World Series, this team finished 51-111 3 years later, one of the ten worst records in history | |
| This team went 86 years without a title. The drought was highlighted by an error from a 1st baseman | |
| Lost in the ALDS 4 straight times in the 2000's | |
| Lost 119 games in 2003, the 2nd worst season in MLB history | |
| Haven't won a World Series in 62 years, just a bit outside. | |
| 0 playoff appearances from 1996-2007 | |
| 41 seasons, and 2 countries later, this team has still not made it to the World Series | |
| Haven't won the World Series since 1954 | |
| Lost 100+ games 4 out of 5 seasons at one point in the 2000's | |
| Have never made the World Series in 33 years of existence | |
| Blew a 7 game division lead with only 17 games left | |
| 2 World Series appearances, going 1-8 in those games, in 41 years of existence | |
| The only team to lose over 100+ games after winning a World Series the previous year | |
| The only team to lose a World Series on purpose | |
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