The Pittsburgh Pirates have not had a winning season since 1992. That is 18 years and counting.
As far as MLB is concerned, the longest losing streak in 23 games held by the 1889 Pittsburgh Alleghenys (soon to be Pirates) and the 1961 Philadelphia Phillies.
The 2002 Oakland Athletics hold the record for the longest Major League Baseball (MLB) winning streak by an American League (AL) team with 20 consecutive wins.
The longest hitting streak in baseball is held by Joe DiMaggio of the New York Yankees, 56 straight games.
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
Pittsburgh pirates at 18 straight and counting
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.
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.
The Chicago Cubs have not won a World Series since 1908.
Cleveland cavaliers 26