Cleveland cavaliers 26
24 games, set by the 1889 Cleveland Spiders. Since 1900, the team with the longest losing streak in baseball was the Philadelphia Phillies, who lost 23 consecutive games from July 26 to August 20 in 1961.
Michael Waltrip had the longest losing streak before winning at the Daytona 500 in 2001.
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