The Pittsburgh Pirates, with 20 losing seasons. They broke their own previous record of 19 consecutive losing seasons. :-(
The Baltimore Orioles?
The Dallas Cowboys
The all-time record for most consecutive losing seasons is held by Prairie View A&M University in Prairie View, Texas. PVAMU, a Division I-AA (FCS) school, compiled 31 consecutive losing seasons from 1976-2006. From 1989-1998, the Panthers lost an NCAA record (all divisions) 80-straight games, nearly doubling second-place Columbia's 44 consecutive losses. The Panthers finally achieved a winning 7-3 record in 2007 before going 9-1 in 2008, and again going 9-1 as well as winning the SWAC championship in 2009. Oregon State University ran up 28 consecutive losing seasons from 1971-1998 to earn the NCAA Division I-A (FBS) record for consecutive losing seasons. During that time the Beavers compiled a 65-238-6 record.
The University of Oklahoma
Rickey Henderson in 25 straight seasons!! Ty Cobb in 24 seasons
Dallas Cowboys holds the record with a winning season every year from 1966 to 1985. It is also the record for most consecutive winning seasons of any professional sports team.
North Carolina, with 31 consecutive 20-win seasons (1970-71 through 2000-01)
Linfield College in McMinnville, OR. 54 consecutive winning seasons as both NAIA and NCAA Division III teams.