Looking Back on Worst Regular Season MLB Teams to Reach Playoffs

As we cross the midway point of the 2023 MLB regular season, we’re once again seeing how all division leaders are not created equal.

Take, for instance, the American League East, where all five of the division’s teams have records above .500.

On the other end of the winning spectrum, you have the AL Central, where Minnesota and Cleveland are befuddling users of legal sports betting apps by currently holding the top spot despite each having a .494 winning percentage.

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The picture is roughly the same in the NL Central, where Cincinnati and Milwaukee are currently the only teams with records above the .500 mark.

With the AL and NL Central being especially down this season, a record just a few games about .500 might be enough to win either division. U.S. Betting Report decided to look back at the worst regular season teams (86 or fewer wins) to reach the postseason since the MLB expanded to three divisions in 1994.

We utilized historical records from MLB.com and Baseball-Reference.com to construct this list.

BetMGM Sportsbooklists Minnesota as the current favorite to win the AL Central at -185, while Milwaukee is the NL Central favorite at +110

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Worst MLB Playoff Teams Since 1995

A year after becoming one of the worst teams to make the playoffs, Tampa Bay is 57-30, leads the AL East and is +450 to win the World Series on U.S. mobile sports betting sites.

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Padres in 2005 Made Surprising Run to Postseason

When it comes to regular season futility among MLB playoff teams, it’s hard to knock off the 2005 San Diego Padres.

The Padres qualified for the postseason despite going 82-80 (.506) — finishing five games ahead of the Arizona Diamondbacks in a rotten NL West division race.

San Diego had one hitter with a .300 or better batting average (Brian Giles) and one starter with an ERA below 3.00 (Jake Peavy) — but still made it to the playoffs.

Unsurprisingly, the Padres’ postseason run was short-lived, with San Diego falling to the St. Louis Cardinals in three games to end its season.

Speaking of St. Louis, the Cardinals are the only team on our list to win it all, doing so in 2006, despite posting a 83-78 (.516) record during the regular season.

That Tony La Russa-coached club defeated the Detroit Tigers in the World Series in five games after defeating the Padres in the NLDS (in four games) and the New York Mets (in seven games) in the NLCS.

Whether this year’s Reds or Twins can do something similar remains to be seen, though there’s nothing saying regular season futility automatically disqualifies a team from getting hot at the right time.

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