Michael Waltrip had the longest losing streak before winning at the Daytona 500 in 2001.
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In 1997, the Cubs started the season 0-14, with the 14 game losing streak being their longest ever.
The Boston Red Sox longest losing streak in club history is 20 games in the 1906 season. It is one game short of the longest losing streak in AL history, held by the Baltimore Orioles who lost 21 consecutive games in the 1988 season.
18 games in 1982
9 as of 8/5/12
11 games in 63-64