No manager ever led a White Sox team into the postseason more than once until Ozzie Guillen did so more than a century into the franchise's history. No manager has ever led the White Sox into the postseason in consecutive years--although Gene Lamont deserves an asterisk for that one. His Sox team won the American League Central in 1993 and was in position to repeat when a labor dispute ended the 1994 season on August 12.
Interestingly, no White Sox team ever qualified for postseason play without finishing in first place until this year. Wild-card playoff berths have been available since 1995, but this year is the first time the Sox have claimed one.
Below is the complete list of White Sox teams in the postseason.
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OZZIE GUILLEN
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1901W. 83 L. 53 .610
Finished first in American League
(No postseason)
1906
W. 93 L. 58 .616
Manager: Fielder Jones
Finished first in American League
Defeated Cubs 4 games to 2 in World Series
1917
W. 100 L. 54 .649
Manager: Pants Rowland
Finished first in American League
Defeated New York Giants 4 games to 2 in World Series
1919
W. 88 L. 52 .629
Manager: Kid Gleason
Best Player: Eddie Cicotte
Finished first in American League
Lost to Cincinnati Reds 5 games to 3 in World Series
1959
W. 94 L. 60 .610
Finished first in American League
Lost to Los Angeles Dodgers 4 games to 2 in World Series
1983
W. 99 L. 63 .611
Finished first in American League West
Lost to Baltimore Orioles 3 games to 1 in A.L. Championship Series
1993
W. 94 L. 68 .580
Finished first in American League West
Lost to Toronto Blue Jays 4 games to 2 in A.L. Championship Series
1994
W. 67 L. 46 .593
Manager: Gene Lamont
Best Player: Frank Thomas
Finished first in American League Central
(No postseason due to dispute between owners and players)
2000
W. 95 L. 67 .586
Best Player: Frank Thomas
Finished first in American League Central
Lost to Seattle Mariners 3 games to 0 in A.L. Division Series
2005
W. 99 L. 63 .611
Finished first in American League Central
Defeated Boston Red Sox 3 games to 0 in A.L. Division Series
Defeated Los Angeles Angels 4 games to 1 in A.L. Championship Series
Defeated Houston Astros 4 games to 0 in World Series
2008
W. 89 L. 74 . 546
Manager: Ozzie Guillen
Finished first in American League Central
Lost to Tampa Bay Rays 3 games to 1 in A.L. Division Series
2020
W. 35 L. 25 .583
Tied for second in American League Central
Lost to Oakland Athletics 2 games to 1 in A.L. Wild Card Series
("Best Player" based on Baseball Reference Wins Above Replacement.)