On September 14, 2011 — With their 3-2 loss to St. Louis, the Pirates extend their record streak of consecutive losing seasons to 19 straight years, the longest in American professional sports history. The Bucs, who led the NL Central by a half-game on July 20, have lost 38 of 54 contests since then, leaving the team with a 67-82 won-loss record.

 


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Sources:
Baseball Reference September 14
National Pastime
Retro Sheet
Hall of Fame
SABR Games Project
Replay The Game