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Flashback: Must-win White Sox games

Quick research (possibly incomplete) indicates the White Sox have played only one max-series playoff game ever: The 6-4 loss to Oakland in Game 3 of the Wild Card Series in 2020. But there are at least three other do-or-die regular…

By Brett Ballantini · South Side Sox

Published: Saturday, 10 October 2026 at 1:19 AM

Key Things to Know

Brett Ballantini examines the Chicago White Sox's past performances in must-win and do-or-die games.
The White Sox's only previous winner-take-all postseason game was a 6-4 loss to Oakland in 2020.
Chicago won the historic 2008 Game 163 tiebreaker against Minnesota 1-0 behind John Danks and Jim Thome.

The Story in 60 Seconds

South Side Sox writer Brett Ballantini reviews the Chicago White Sox's history in winner-take-all and must-win contests ahead of their decisive ALDS Game 5 against Cleveland. The franchise has historically played only one true max-series postseason game, alongside two famous do-or-die regular season finales.

The retrospective highlights a 7-0 loss to the Detroit Tigers in 1908, the famed 1-0 "Blackout Game" tiebreaker victory over the Minnesota Twins in 2008, and a 6-4 Wild Card Series Game 3 defeat to the Oakland Athletics in 2020.

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Flashback: Must-win White Sox games

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