I've had a 110 win team knocked out of the semis. I've also had an 83 win team steal a championship.
Similar things can and do happen in real baseball. The 1906 Cubs won 116 games but lost the WS to the crosstown "Hitless Wonders." The 111 win 1954 Cleveland Indians lost the WS to the Giants. The 116 win 2001 Mariners were knocked out of the ACLS by the Yankees. Between 1993 and 2013 the Braves won more than 100 games six times, but none of those teams won a WS. Their only World Championship in that period went to a 90 win team.
Meanwhile, the 1987 Twins won only 85 games in the regular season, but took the WS. And the 2006 Cardinals took the Series with just 83 wins.
In a game (real or simulated) where a strong modicum of chance mixes with skill, anything can happen, particularly in a short series. And in SOM we've had thousands of leagues instead of a little more than 200, so the chances for strange happenings is magnified.
That doesn't make it hurt any the less, though. I'm still getting over that wipe-out of my 110 win team in the semis. And I'm annoyed that my 100+ win teams have performed worse, overall, than my 90-94 win teams. (Yes, I've counted!)