11 games in 63-64
The Chicago Cubs 2008 longest losing streak was 6 games between August 30 and September 6.
Michael Waltrip had the longest losing streak before winning at the Daytona 500 in 2001.
Cleveland cavaliers 26
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
Prairie View A&M (80)
The team to have the longest losing streak in NFL history is-The Tampa Bay Buccaneers. In 1976, 0-14; in 1977 they started off with a 12 straight losing streak, having the NFL's longest losing streak of 26 games. They did, however, manage to win two of their games at their season's end, ending their season with a record of 2-12.
The Seattle Mariners lost 14 games in a row from 9-2-1992 to 9-18-1992; their longest losing streak as of 7-20-2011.
The longest losing streak is 23 games in a row by 95-96 Grizzlies and 97-98 Nuggets.
Make that 18 seasons (1992 - 2010) and counting.
That would be his current losing streak of 104 races.
The Chicago Cubs have not won a World Series since 1908.