The Anaheim Angels and the Philadelphia Phillies share the record for the longest losing streak within the 1999 season at 11 straight games.
| Team | Losing Streak | Start | End | Avg Margin of Defeat | |
|---|---|---|---|---|---|
| 1 | Anaheim Angels | 11 | Jul 16 | Jul 26 | 3.5 runs |
| Philadelphia Phillies | 11 | Sep 4 | Sep 14 | 6.0 runs | |
| 3 | Baltimore Orioles | 10 | Jun 23 | Jul 3 | 2.0 runs |
| Florida Marlins | 10 | Jun 14 | Jun 25 | 3.0 runs | |
| 5 | Anaheim Angels | 9 | Aug 24 | Sep 2 | 2.9 runs |
| Colorado Rockies | 9 | Jun 24 | Jul 2 | 5.7 runs | |
| Detroit Tigers | 9 | Jul 26 | Aug 5 | 4.1 runs | |
| Kansas City Royals | 9 | May 29 | Jun 7 | 3.2 runs | |
| 9 | Florida Marlins | 8 | Apr 28 | May 5 | 3.6 runs |
| Minnesota Twins | 8 | Sep 25 | Oct 2 | 3.4 runs | |
| New York Mets | 8 | May 28 | Jun 5 | 2.8 runs | |
| San Diego Padres | 8 | Jul 23 | Jul 31 | 2.8 runs | |
| 13 | Anaheim Angels | 7 | Aug 6 | Aug 13 | 4.0 runs |
| Chicago White Sox | 7 | Aug 5 | Aug 11 | 4.7 runs | |
| Florida Marlins | 7 | Aug 18 | Aug 27 | 3.9 runs | |
| Florida Marlins | 7 | Sep 10 | Sep 16 | 3.4 runs | |
| Montreal Expos | 7 | May 10 | May 17 | 3.3 runs | |
| Montreal Expos | 7 | Apr 19 | Apr 29 | 1.6 runs | |
| New York Mets | 7 | Sep 21 | Sep 28 | 2.4 runs | |
| Philadelphia Phillies | 7 | Aug 28 | Sep 2 | 3.1 runs | |
| San Diego Padres | 7 | Aug 7 | Aug 13 | 3.9 runs | |
| Seattle Mariners | 7 | Jul 6 | Jul 16 | 4.6 runs | |
| St. Louis Cardinals | 7 | Aug 23 | Aug 30 | 2.6 runs | |
| Tampa Bay Devil Rays | 7 | May 22 | May 29 | 4.7 runs | |
| Tampa Bay Devil Rays | 7 | Jun 4 | Jun 11 | 4.6 runs | |
| Toronto Blue Jays | 7 | Aug 12 | Aug 18 | 3.6 runs | |
| 27 | Anaheim Angels | 6 | Jun 13 | Jun 19 | 4.0 runs |
| Baltimore Orioles | 6 | Jul 29 | Aug 3 | 4.3 runs | |
| Baltimore Orioles | 6 | May 10 | May 15 | 4.0 runs | |
| Baltimore Orioles | 6 | Apr 16 | Apr 22 | 3.2 runs | |
| Chicago Cubs | 6 | Aug 7 | Aug 13 | 3.8 runs | |
| Chicago Cubs | 6 | Sep 7 | Sep 12 | 3.5 runs | |
| Chicago White Sox | 6 | Sep 6 | Sep 11 | 4.7 runs | |
| Colorado Rockies | 6 | Jul 23 | Jul 28 | 4.3 runs | |
| Detroit Tigers | 6 | Apr 6 | Apr 12 | 5.5 runs | |
| Kansas City Royals | 6 | Aug 27 | Sep 1 | 3.3 runs | |
| Kansas City Royals | 6 | Jul 7 | Jul 16 | 2.5 runs | |
| Los Angeles Dodgers | 6 | Jun 27 | Jul 3 | 4.2 runs | |
| Milwaukee Brewers | 6 | Jul 31 | Aug 6 | 5.2 runs | |
| Minnesota Twins | 6 | May 14 | May 19 | 5.2 runs | |
| Minnesota Twins | 6 | May 5 | May 10 | 3.3 runs | |
| Minnesota Twins | 6 | Sep 12 | Sep 18 | 2.7 runs | |
| Montreal Expos | 6 | Jul 10 | Jul 18 | 3.3 runs | |
| Oakland Athletics | 6 | May 18 | May 23 | 5.7 runs | |
| Oakland Athletics | 6 | Jun 23 | Jun 29 | 1.3 runs | |
| Texas Rangers | 6 | Oct 1 | Oct 9 | 4.5 runs | |
| Toronto Blue Jays | 6 | Sep 14 | Sep 21 | 2.8 runs | |
| 48 | Anaheim Angels | 5 | Apr 17 | Apr 22 | 2.0 runs |
| Atlanta Braves | 5 | Jul 17 | Jul 21 | 3.2 runs | |
| Boston Red Sox | 5 | Jun 5 | Jun 9 | 4.8 runs | |
| Chicago Cubs | 5 | Aug 15 | Aug 20 | 4.4 runs | |
| Chicago Cubs | 5 | Jun 16 | Jun 20 | 3.6 runs | |
| Chicago Cubs | 5 | Jun 9 | Jun 14 | 3.0 runs | |
| Chicago White Sox | 5 | May 16 | May 22 | 6.4 runs | |
| Chicago White Sox | 5 | Aug 30 | Sep 3 | 5.0 runs | |
| Chicago White Sox | 5 | Apr 7 | Apr 13 | 4.4 runs | |
| Cleveland Indians | 5 | Jul 21 | Jul 25 | 4.8 runs | |
| Colorado Rockies | 5 | Aug 6 | Aug 10 | 2.8 runs | |
| Detroit Tigers | 5 | May 9 | May 15 | 3.4 runs | |
| Florida Marlins | 5 | Jul 31 | Aug 5 | 2.6 runs | |
| Kansas City Royals | 5 | Jun 12 | Jun 16 | 2.6 runs | |
| Kansas City Royals | 5 | Aug 20 | Aug 24 | 2.4 runs | |
| Los Angeles Dodgers | 5 | Jul 21 | Jul 24 | 3.4 runs | |
| Milwaukee Brewers | 5 | Aug 20 | Aug 24 | 4.4 runs | |
| Milwaukee Brewers | 5 | Jul 23 | Jul 27 | 3.6 runs | |
| Milwaukee Brewers | 5 | May 25 | May 29 | 3.2 runs | |
| Milwaukee Brewers | 5 | Apr 27 | May 1 | 2.2 runs | |
| Minnesota Twins | 5 | May 25 | May 30 | 4.4 runs | |
| Minnesota Twins | 5 | Aug 16 | Aug 20 | 4.2 runs | |
| Minnesota Twins | 5 | Apr 21 | Apr 25 | 2.8 runs | |
| Montreal Expos | 5 | Jul 1 | Jul 6 | 4.6 runs | |
| Montreal Expos | 5 | Jun 15 | Jun 20 | 3.6 runs | |
| New York Yankees | 5 | May 11 | May 15 | 3.8 runs | |
| Pittsburgh Pirates | 5 | May 17 | May 21 | 4.2 runs | |
| Pittsburgh Pirates | 5 | Jul 19 | Jul 23 | 3.2 runs | |
| San Diego Padres | 5 | May 22 | May 26 | 2.6 runs | |
| San Diego Padres | 5 | Apr 28 | May 2 | 1.4 runs | |
| San Francisco Giants | 5 | Sep 23 | Sep 28 | 4.6 runs | |
| San Francisco Giants | 5 | Jun 21 | Jun 26 | 3.4 runs | |
| San Francisco Giants | 5 | May 27 | May 31 | 1.8 runs | |
| Seattle Mariners | 5 | Aug 4 | Aug 8 | 3.8 runs | |
| St. Louis Cardinals | 5 | Sep 22 | Sep 27 | 2.4 runs | |
| Tampa Bay Devil Rays | 5 | Jul 30 | Aug 3 | 3.6 runs | |
| Tampa Bay Devil Rays | 5 | Sep 10 | Sep 14 | 3.2 runs | |
| Tampa Bay Devil Rays | 5 | Jul 21 | Jul 25 | 1.6 runs | |
| Toronto Blue Jays | 5 | Jun 7 | Jun 12 | 4.8 runs |
In the 1999 MLB season, there were no losing streaks that were in the all time top 50 losing streaks in the same season.
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All MLB stats, streaks, droughts and records are updated based on games played on or before May 17, 2024.
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