Wartburg Wrestling in Division III has won 20 consecutive IIAC Titles and has not lost a IIAC dual meet since 1993.
The longest current playoff streak in professional sports belongs to the NBA's San Antonio Spurs, who made the playoffs for 22 consecutive seasons from 1998 to 2019.
the 2009 nets went 0-18 till finally winning one
cleveland indians
Trinity squash has a won 221 games in a row. After that I would have to go with UCLA 88 game winning streak followed by the current Uconn womens streak of 78 games
Don Criqui has the longest tenure in sports radio.
Johns Hopkins University, Men's Lacrosse
They are Division I in only Mens' baseball and Womens' Lacrosse. All other sports are Division II. They are considering going to Division I for all sports.
NCAA Division II.
The City of Cleveland has 3 professional sports teams and has not won a Championship since 1964 making them the city that has gone the longest without winning a Championship. The Chicago Cubs of Major League Baseball are in the midst of a 102 year World Series Championship drought. (1908 was their last W.S. Title) The Cubs haven't even appeared in a World Series game since 1945. This is by far the longest individual drought in all of sports.
Sports & life both have winning & losing
PGA Golf has the longest season. It is active 93% of the year.