In the world of Major League Baseball (MLB), losing streaks are inevitable, but with a chance to play nearly every day and with the nature of a 162-game regular season, losing streaks tend not to be as prolonged as the NBA, for example. Some teams, however, have endured historically significant slumps. Here, we delve into the longest MLB losing streaks in history (modern era – since 1900), highlighting the teams that experienced these challenging periods.

1: Philadelphia Phillies: 23 Games (1961)

The Philadelphia Phillies experienced the longest losing streak in MLB history during the 1961 season. From July 29 to August 20, the Phillies lost 23 consecutive games. This streak remains the longest not just in franchise history but in the league as a whole. The team struggled with pitching and defense throughout the streak, leading to numerous losses. Despite this rough patch, the Phillies eventually ended the streak with a 7-4 victory over the Milwaukee Braves, marking the end of the longest MLB losing streak ever recorded.

2=: Baltimore Orioles – 21 Games (1988)

The Baltimore Orioles’ 1988 season began in the worst possible way, with a 21-game losing streak. This streak is the longest at the start of a season in MLB history. The Orioles struggled in all aspects of the game, from pitching to hitting, and it wasn’t until April 29 that they secured their first win of the season against the Chicago White Sox. The 1988 Orioles finished the season with a 54-107 record, but the losing streak at the start remains a memorable low point in the franchise’s history.

2=: Chicago White Sox: 21 Games (2024)

Between July 10th and August 5th of 2024 the Chicago White Sox went on a 21-game losing streak that would ultimately cost the job of manager Pedro Grifol and several of his coaching staff. It was a particularly tough period for the team, as they struggled with injuries and underperformance, and on top of that most of their relevant roster was poached at the trade deadline.

Now the White Sox have added one very unwelcome record to their storied history: tying the AFL losing streak record with the above-named Orioles.

4=: Boston Red Sox – 20 Games (1906)

The Boston Red Sox, then known as the Boston Americans, endured a 20-game losing streak in 1906. This streak, which stretched from May 1 to May 25, is one of the longest in the history of the storied franchise. During this period, the team struggled to score runs and experienced poor pitching performances. The 1906 season ended with a 49-105 record, but the 20-game losing streak remains a significant part of the Red Sox’s history.

4=: Oakland Athletics – 20 Games (1916 and 1943)

The Oakland Athletics hold the unique distinction of having two separate 20-game losing streaks in their history. The first occurred in 1916 when the team was based in Philadelphia and known as the Philadelphia Athletics. This streak ran from July 21 to August 8, during a season in which the team finished with a 36-117 record, one of the worst in MLB history.

The second 20-game losing streak happened in 1943, during a period when the Athletics were struggling both on and off the field. This streak, from August 7 to August 24, was part of a season that saw the team finish with a 49-105 record. These two streaks are a testament to the challenges the Athletics faced during those periods.