5 Biggest Losing Streaks in Baseball History

By: Dave Roos

Billy and Cal Ripken, Jr. of the Baltimore Orioles survey the field during the ill-fated 1988 season. See more sports pictures.
Andrew D. Goldstein/Getty Images

Americans love a good losing streak. We thrill at the improbability of it. We ogle the emotional wreckage like it was a 23-car pileup. In a nation that usually roots for the underdog, sometimes we just want them to get pummeled -- again, and again, and again. Until it seems they can't possibly lose another, which of course they do, and then we quietly cheer.

Baseball has produced some monumental and memorable losing streaks. Longtime fans of the following teams still carry the memories of these streaks like scars. World Series championships come and go, but the slow burn of a 20-game losing streak is seared into the heart forever. You can't escape the nagging fear that the impossible will somehow happen again, and a month of summer with pass without a "W."


And now, our list of the five longest losing streaks in baseball history, starting with a summer at the turn of the 20th century that Bostonians would rather forget.

5: Boston's Twin Streaks

Boston is famously cursed as a baseball city. The Curse of the Bambino, as it was known, held the Red Sox without a pennant from 1918 until 2004. What makes the curse so cursed is that before the 86-year dry spell, the Red Sox were arguably the best team in baseball, winning the first World Series in 1903 and picking up four more titles in 1912, 1915, 1916 and 1918. The only truly miserable year was 1906. And boy was it miserable.

In 1906, there were two major league clubs in Boston, the Braves (aka the Beaneaters) and the Americans, the team that became the Red Sox in 1908. Both teams tallied record-breaking losing streaks in 1906, making Boston the most joyless place to watch baseball outside of Mudville.


The Americans were the worst of the worst that year, with a 20-game losing streak and a phenomenal 49-105 record. The Braves put up a fight, though, with a 19-game losing streak and more than 100 losses for the season [source: Gonzalez].

Next on our list of the biggest losers is another double streak, this time from the same team.

4: The 1916 and 1943 Philadelphia Athletics

Legendary Philadelphia Athletics manager Connie Mack, circa 1936.
Legendary Philadelphia Athletics manager Connie Mack, circa 1936.
Louis Van Oeyen/Getty Images Sport

Connie Mack is easily one of the greatest managers in baseball history. The Hall of Fame skipper coached the Philadelphia Athletics to nine American League pennants and five World Series titles. Incredibly, his career in Philadelphia spanned 50 years from 1901 to 1950. Even more incredible, this gold-plated winner and baseball legend also holds the record for two of the longest losing streaks in the game's history.

In 1916, just two years after he took the Athletics to the World Series, Mack presided over one of the most dreadful end-of-season performances by any pro baseball club, before or since. The A's dropped 56 out of their last 60 games, including a 20-game losing streak [source: Gonzalez]. The final 1916 record was 36-117. It would signal the start of a seven-year slump in which the Athletics came in last in the American League every season.


While the rest of the country slogged through the Depression, Athletics fans had a lot to cheer for in 1929 and 1930, when Mack lead his Athletics to back-to-back World Series titles. But as Mack is famously quoted as saying, "You can't win them all." And from the mid-1930s through the mid-1940s, the A's lost many more than they won. In 1943, Mack matched his 1916 season with another 20-loss streak, ending the season at 49-105 [source: Baseball-Reference].

3: 1988 Baltimore Orioles

Few people expected the 1988 Baltimore Orioles to be World Series contenders, but no one could have predicted their astonishingly bad start to the season. Cal Ripken Sr. was at the helm of the struggling Orioles franchise, which finished 13th in the American League in 1987, ending the season with a dismal 42 losses over their last 56 games. That's momentum, all right, just the wrong kind of momentum [source: Washington Post].

For the 1988 season opener, a crowd of 52,395 packed Memorial Stadium in Baltimore to watch their hopes of redemption crushed by a 12-0 slaughter at the hands of the Milwaukee Brewers. The embarrassing loss included a botched bunt, a run scored from second on an infield hit, two wild pitches, two hit batsmen and even a rare stolen base by the Brewers: home [source: Justice].


Somehow, things only got worse from there. The Orioles lost their next game, then the next, then the next. After the seventh consecutive loss of the season, the Orioles management fired Cal Ripken, Sr., despite the awkward fact that Ripken's two sons were playing shortstop and second base [source: Justice].

By the time the cursed Orioles faced the Minnesota Twins on April 26, 1988, they were a national media sensation for all of the wrong reasons. They had lost an unprecedented 19 of their first 19 games. It seemed quite possible that they would never win, ever. Still, the Orioles kept hope alive. Cases of champagne were on ice in the locker room. President Ronald Reagan even called the team before the game to wish them luck. But did they win one for the Gipper? Nah.

The Orioles finally snapped their headline-grabbing losing streak with a 9-0 drubbing of the Chicago White Sox, 26 days and 21 losses into the season [source: Justice]. The mood in the clubhouse was relief, not elation. No one even bothered to crack open the champagne.

"The worst we could do is lose one more," said Orioles pitcher Mark Williamson. "I'm relieved, but we have to keep it in perspective. It's not like we just won the seventh game of the World Series. Maybe we won't be so much of a household name now" [source: Justice].

To top the incredibly poor performance of the 1988 Orioles, we have to travel back to the 1961 Philadelphia Phillies.

2: 1961 Philadelphia Phillies

The Philadelphia Phillies celebrate after winning the 2008 World Series – a far cry from the losing streaks of old.
The Philadelphia Phillies celebrate after winning the 2008 World Series – a far cry from the losing streaks of old.
Ron Tringali/Getty Images

In late July of 1961, a very young Philadelphia Phillies team went on a five-game losing streak before winning the second game of a double-header against the San Francisco Giants on July 28. A five-game slump isn't great news, but it's nothing to cry in your beer about. What came next, though, had Phillies fans sobbing into their Yuengling for three straight weeks.

From July 28 through August 20, the Phillies lost 23 straight games [source: Donaghy]. If you overlooked that lone "W" against the Giants, it was more like 28 games. The colossal losing streak still stands as the longest in major league history since the advent of the World Series in 1903.


The '61 Phillies were young, but they weren't terrible. They just had a very, very bad run. During the streak, they batted a collective .248 and couldn't seem to convert with runners in scoring position. Many of the games could have gone either way, though: Eight of the matches, painfully enough, were lost by a single run [source: Philly.com].

Phillies manager Gene Mauch loved his players, but hated losing. After one crushing loss, he smashed the dugout lights. When they installed protective cages around the lights, he took them out with a bat. When one of his players was tagged hard at home, Mauch led the rest of the team in a bench-clearing brawl [source: Donaghy].

Phillies fans can be brutal, but they are nothing if not loyal. When the Phillies finally broke the cursed streak, they boarded a late flight back to Philadelphia, arriving close to midnight. From their windows, the team saw a crowd assembled at the gate. A player joked that that someone was selling rocks to the crowd for a dollar a bucket.

To the Phillies' great surprise, the crowd of 2,000 was there to cheer the return of their triumphant heroes. A brass band played as the crowd lifted the tortured Phillies manager Gene Mauch on their shoulders and paraded him for a long-awaited victory lap [source: Philly.com].

1: 1899 Cleveland Spiders

Baseball fans have terrific long-term memories, particularly for the worst teams to ever play the game. It turns out that two of the longest losing streaks in Major League Baseball history didn't happen in this century, or the last one for that matter. The shame of the longest losing streak in baseball (24 games!) belongs to the atrocious Cleveland Spiders of 1899, who broke the 23-game record previously held by the miserable Pittsburgh Alleghenys squad of 1890.

You might not recognize the names, but these two clubs were legitimate National League teams back in the late 19th century. The Alleghenys earned the nickname "the Pirates" in 1891 when they "stole" (signed, technically) a prized second baseman from the Philadelphia Athletics [source: Pirates]. The Cleveland Spiders, however, didn't evolve into the Cleveland Indians of today. Instead, the Spiders were born in 1879 and died in 1899 after playing arguably the worst season of baseball in the game's history [source: Indians].


The most important number here is 24, which is the number of consecutive losses that the Spiders endured during that fateful 1899 season. Equally impressive in shamefulness is the team's season record of 20 wins and 134 losses. The blame for the appalling record certainly rests on the players, but also on the team's owner, who gutted the club of its best players and sent them to his new team in St. Louis [source: Indians].

The 1890 Pittsburgh Alleghenys suffered a similar fate. After the close of the 1889 season, an Alleghenys star player named Ned Hanlon defected for the Pittsburgh Burghers of the newly created Player's League and took all but four of the Alleghenys' roster with him [source: Dreker]. The abandoned Alleghenys not only lost 23 in a row in 1890, but amassed a demoralizing 23-113 record.

The Burghers folded after only one season, and Hanlon and his fellow defectors went back to the Alleghenys and returned the club to its former pretty-goodness. The 1899 Spiders weren't so lucky: After their record-breakingly bad season, the National League squashed the lowly Spiders for good [source: Indians].

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Author's Note: 5 Biggest Losing Streaks in Baseball History

I like a good losing streak as much as the next guy. Call me sadistic, but I love to see the hope in the eyes of the cursed team as they take the field, confident that this will be the day that everything changes. I love the stock quotes from the players and management after another loss. "We're just taking it one game at a time." "This team knows how to win. We just need to make it happen." Maybe we love losing streaks so much, because we know they will end. They have to. In sports, if not always in life, there's always hope for redemption, even during the worst of seasons.

Related Articles

  • Baseball-Reference.com. "Connie Mack" (July 24, 2011) http://www.baseball-reference.com/managers/mackco01.shtml
  • Donaghy, Jim. Los Angeles Times. "1961 Phillies: They Made Their Mark in Baseball History with 23 Consecutive Losses." May 3, 1988 (July 24, 2011) http://articles.latimes.com/1988-05-01/sports/sp-3190_1_philadelphia-phillies
  • Dreker, John. Pirates Prospects. "Ned Hanlon." February 6, 2011 (July 24, 2011) http://www.piratesprospects.com/2011/02/ned-hanlon.html
  • Gonzalez, Alden. MLB.com. "Longest single-season losing streaks by club." July 27, 2011 (July 24, 2011) http://mlb.mlb.com/news/print.jsp?ymd=20110727&content_id=22370240&c_id=mlb
  • Indians.com. "Indians History Overview: The early years" (July 24, 2011) http://cleveland.indians.mlb.com/cle/history/cle_history_overview.jsp
  • Justice, Richard. Washington Post. "Orioles Fire Cal Ripkin Sr." April 13, 1988 (July 24, 2011) http://www.washingtonpost.com/wp-srv/sports/orioles/longterm/memories/1988/articles/ripfired.htm
  • Justice, Richard. Washington Post. "Orioles Lose Opener to Brewers, 12-0." April 5, 1988 (July 24, 2011) http://www.washingtonpost.com/wp-srv/sports/orioles/longterm/memories/1988/articles/game1.htm
  • Justice, Richard. Washington Post. "Nightmare's Over As Orioles Wake, 9-0." April 30, 1988 (July 24, 2011) http://www.washingtonpost.com/wp-srv/sports/orioles/longterm/memories/1988/articles/game22.htm
  • Philly.com. "Remember 1961 Phillies' 23-game losing streak." April 5, 2011 (July 24, 2011) http://articles.philly.com/2011-08-05/sports/29854816_1_ruben-amaro-phillies-gene-mauch
  • Pirates.com. "Timeline: 1887-1900" (July 24, 2011) http://pittsburgh.pirates.mlb.com/pit/history/timeline.jsp
  • Washington Post. "The 1988 Orioles: A Season to Forget" (July 24, 2011) http://www.washingtonpost.com/wp-srv/sports/orioles/longterm/memories/1988/1to10.htm