The longest losing streak is 23 games in a row by 95-96 Grizzlies and 97-98 Nuggets.
That would be his current losing streak of 104 races.
Michael Waltrip had the longest losing streak before winning at the Daytona 500 in 2001.
New Jersey Nets with an 0-18 losing streak
The Chicago Cubs 2008 longest losing streak was 6 games between August 30 and September 6.
The NFL team that holds the record for the longest losing streak are the Tampa Bay Buccaneers. In 1976, they lost every game they played that season. Their record is a 26 game losing streak.
10 game loosing streak
In 1997, the Cubs started the season 0-14, with the 14 game losing streak being their longest ever.