Longest Losing Streaks In MLB History

Many baseball fans remember 1961 as the year that Roger Maris broke Babe Ruth’s single-season home run record, but that wasn’t the only record to fall that summer.

Over in the National League, the Philadelphia Phillies set a new record for futility.

The Phillies were already on the downswing heading into 1961. They were coming off three straight last-place finishes in the eight-team National League, with their winning percentage declining each season.

Those trends continued in 1961, with Philadelphia again finishing last as its record continued to worsen. The Phillies lost a whopping 107 games – their most since 1945.

That included a horrific losing streak in the middle of summer where the club went nearly a month between wins. Starting on July 29, Philadelphia went winless until Aug. 20, when it finally won the second game of a doubleheader against the Milwaukee Braves. The win ended a 1-28 stretch for the Phillies, which included 23 consecutive losses where the team averaged just 2.35 runs per game.

More than 60 years later, that’s still the all-time record.

The Baltimore Orioles’ losing streak is especially memorable because it happened at the beginning of the year, making it the worst start to a season in MLB history.

Despite having perennial All-Stars Cal Ripken Jr., Eddie Murray and Fred Lynn in their lineup, the Orioles opened the season with 21 straight losses. Manager Cal Ripken Sr. was fired after just six games, but Baltimore still lost the next 15 under new skipper Frank Robinson.

The Orioles didn’t win their first game until April 29 — 25 days after Opening Day. They were outscored 129 to 44 over the course of the streak and averaged just 2.10 runs per game.

Baltimore went 67-95 the year before, so its dismal start wasn’t a complete surprise. The Orioles never recovered, ending up with the worst record in baseball (54-107).

It’s been a remarkable fall from grace for the White Sox, who looked like one of the best young teams in baseball just a few years ago. Chicago’s winning percentage has declined every year since 2020 as its roster has slowly been decimated by trades, injuries and bad signings.

Coming off 101 losses in 2023, the White Sox weren’t expected to be good this year. However, I’m not sure anyone expected them to be this bad.

Chicago started the year by losing 22 of its first 25 games, immediately eliminating any hope of contention. Since then, its season has been a long, slow, painful death march.

Like many historic losing streaks, this one was defined by a combination of horrendous hitting, pitching and defense. The White Sox averaged a paltry 2.33 runs per game while allowing 6.48 runs per game during their epic slide.

The first modern MLB team to lose at least 20 straight games was the Boston Americans, who changed their name to the Red Sox two years later.

The Americans’ collapse in 1906 was as swift as it was shocking. Boston had a winning record in 1905 and was only three years removed from winning the first World Series ever played.

The Americans started the season slowly, going 6-7 in April before completely collapsing in May. They lost 20 straight games to start the month, all at home.

Boston’s offense floundered during the streak (2.65 runs per game), but the real issue was its pitching staff. Not even an aging Cy Young could stop the Americans from surrendering 6.8 runs per game during their skid – an extremely high number in the Deadball era.

Similar to the Americans a decade before them, the Philadelphia Athletics suddenly cratered after a period of success. The A’s went from winning the AL pennant in 1914 to 109 losses in 1915 as manager/owner Connie Mack was forced to sell off his stars due to financial issues.

Philadelphia bottomed out in 1916, losing a franchise-record 117 games. The A’s were especially bad over a two-month stretch in the middle of the season, going 4-56 from June 3 to Aug. 8.

The lowlight was a 20-game losing streak from July 21 to Aug. 8 that cemented Philadelphia’s status as one of the worst teams in MLB history. The punchless A’s scored just 37 runs during the streak – a mere 1.85 per game.

The A’s matched their own futility in 1943, losing 20 consecutive games once again. They are the only MLB franchise with multiple 20-game losing streaks.

At 80 years old, Mack was still at the helm. His roster was once again stripped of talent, this time by World War II. Only one player in Philadelphia’s lineup had more than three home runs that year.

The A’s endured their 10th straight losing season, finishing in last place at 49-105. They actually started the season fairly well, playing above .500 into mid-June before the wheels came off.

The death knell was a 20-game losing streak in August, most of which occurred during a lengthy road trip (back when teams still traveled exclusively by train). That must have been fun.

The Montreal Expos were an expansion team in 1969, and they did not make a good first impression.

Expansion teams typically struggle due to insufficient talent, but the Expos were particularly bad. They went 52-110 and just couldn’t seem to catch any breaks, going 16-29 in one-run games and 0-12 in extra innings.

Montreal had no illusions about contending, crashing and burning almost immediately. The Expos lost 20 straight from May 13 to June 7, dooming their inaugural season basically from the start.

When we put together our MLB bet tips before the season, we forgot a very important one: always bet against the White Sox.

At 28-88 entering play on Aug. 7, they’ve already clinched a losing record and are on pace to have the worst record in modern MLB history (since 1900). If Chicago maintains its current winning percentage, it will finish at 39-123 – worse than the infamous 1962 New York Mets (40-120).

Not surprisingly, the White Sox have been underdogs in nearly all of their games this year. They’ve been underdogs in 109 of their 116 games so far and are 24-85 in those contests, making them a terrible investment even at plus odds.

Chicago has been better against the runline (baseball’s version of a spread), going 49-67. However, it’s still wise to bet against the White Sox, as they’ve been outscored by an average of 2.13 runs per game, well above the standard runline of 1.5 runs.

Given the state of Chicago’s roster, don’t expect a major turnaround anytime soon. The White Sox were already a bad team before trading away most of their talented players at the trade deadline. Chicago dealt three of its top hitters (Eloy Jimenez, Tommy Pham and Paul DeJong), one of its best starting pitchers (Erick Fedde) and two of its most reliable relievers (Michael Kopech and Tanner Banks).

The White Sox are essentially a minor league team at this point and have nothing to play for, making them a great target for MLB bettors going forward.