In 1988 the Baltimore Orioles lost 21 straight games to start the season. It was a historically disastrous start to a season and the lovely Grant Brisbee wrote all about it earlier this week:
Opening Day wasn’t ruined when the 1988 Orioles lost, a loss that began their 21-game losing streak. The larger crime was committed against opening week, opening fortnight, and the entire opening month of April. The Orioles opened the season by setting an awful record that was so unbreakable, the universe rewarded them with a much better unbreakable record just a few years later.