The Cleveland Spiders had the longest losing streak within the 1899 regular season at 24 straight games. During this streak they lost to their opponents by an average of 5.9 runs. The streak started on Aug 26, 1899 and ended on Sep 16, 1899.
| Team | Losing Streak | Start | End | Avg Margin of Defeat | |
|---|---|---|---|---|---|
| 1 | Cleveland Spiders | 24 | Aug 26 | Sep 16 | 5.9 runs |
| 2 | Cleveland Spiders | 16 | Sep 18 | Oct 15 | 6.9 runs |
| 3 | Cleveland Spiders | 14 | Jul 1 | Jul 15 | 5.5 runs |
| 4 | Cleveland Spiders | 13 | May 31 | Jun 14 | 5.9 runs |
| 5 | Washington Senators | 12 | Sep 20 | Oct 3 | 4.8 runs |
| 6 | Cleveland Spiders | 11 | Aug 6 | Aug 19 | 7.3 runs |
| Cleveland Spiders | 11 | May 3 | May 15 | 4.8 runs | |
| Washington Senators | 11 | May 1 | May 13 | 4.8 runs | |
| 9 | New York Giants | 10 | Jul 23 | Aug 4 | 2.6 runs |
| Washington Senators | 10 | Jun 21 | Jul 2 | 3.4 runs | |
| 11 | New York Giants | 9 | Aug 30 | Sep 7 | 4.1 runs |
| 12 | Brooklyn Superbas | 8 | Jun 26 | Jul 5 | 3.6 runs |
| Cleveland Spiders | 8 | Jul 21 | Aug 1 | 4.1 runs | |
| Louisville Colonels | 8 | May 26 | Jun 2 | 2.5 runs | |
| New York Giants | 8 | Jun 29 | Jul 10 | 3.4 runs | |
| Washington Senators | 8 | Jun 9 | Jun 19 | 4.2 runs | |
| Washington Senators | 8 | Aug 9 | Aug 19 | 3.8 runs | |
| 18 | Cincinnati Reds | 7 | Jun 2 | Jun 9 | 3.4 runs |
| Cleveland Spiders | 7 | Jun 17 | Jun 24 | 4.4 runs | |
| New York Giants | 7 | Sep 30 | Oct 7 | 5.7 runs | |
| New York Giants | 7 | May 10 | May 19 | 5.0 runs | |
| 22 | Louisville Colonels | 6 | Jun 8 | Jun 15 | 3.0 runs |
| Philadelphia Phillies | 6 | Jul 20 | Jul 25 | 4.2 runs | |
| Pittsburgh Pirates | 6 | Sep 12 | Sep 16 | 3.0 runs | |
| Pittsburgh Pirates | 6 | Apr 17 | Apr 25 | 1.8 runs | |
| St. Louis Perfectos | 6 | Aug 2 | Aug 6 | 4.0 runs | |
| 27 | Baltimore Orioles | 5 | Aug 30 | Sep 4 | 2.8 runs |
| Chicago Orphans | 5 | Aug 12 | Aug 17 | 4.4 runs | |
| Cincinnati Reds | 5 | Aug 16 | Aug 20 | 5.0 runs | |
| Cincinnati Reds | 5 | Jul 5 | Jul 9 | 3.0 runs | |
| Louisville Colonels | 5 | May 18 | May 23 | 5.4 runs | |
| New York Giants | 5 | Jun 14 | Jun 19 | 2.2 runs | |
| Philadelphia Phillies | 5 | May 15 | May 22 | 2.4 runs | |
| Pittsburgh Pirates | 5 | Jun 20 | Jun 26 | 2.8 runs | |
| Washington Senators | 5 | Apr 19 | Apr 24 | 9.2 runs | |
| Washington Senators | 5 | May 30 | Jun 2 | 2.4 runs | |
| 37 | Baltimore Orioles | 4 | Jun 21 | Jun 25 | 3.8 runs |
| Baltimore Orioles | 4 | May 2 | May 5 | 3.5 runs | |
| Boston Beaneaters | 4 | Apr 27 | May 1 | 6.5 runs | |
| Chicago Orphans | 4 | Sep 30 | Oct 3 | 5.8 runs | |
| Chicago Orphans | 4 | Aug 24 | Aug 28 | 4.0 runs | |
| Chicago Orphans | 4 | May 23 | May 26 | 4.0 runs | |
| Chicago Orphans | 4 | Aug 20 | Aug 23 | 3.0 runs | |
| Chicago Orphans | 4 | Jul 28 | Jul 31 | 2.5 runs | |
| Chicago Orphans | 4 | Apr 22 | Apr 25 | 1.8 runs | |
| Cincinnati Reds | 4 | Jun 15 | Jun 19 | 6.0 runs | |
| Cincinnati Reds | 4 | May 25 | May 28 | 5.0 runs | |
| Cincinnati Reds | 4 | Jul 12 | Jul 17 | 2.8 runs | |
| Cleveland Spiders | 4 | Apr 15 | Apr 21 | 6.5 runs | |
| Cleveland Spiders | 4 | Aug 20 | Aug 24 | 6.0 runs | |
| Cleveland Spiders | 4 | Jul 18 | Jul 20 | 4.5 runs | |
| Cleveland Spiders | 4 | Aug 2 | Aug 5 | 4.0 runs | |
| Louisville Colonels | 4 | Oct 6 | Oct 13 | 4.0 runs | |
| Louisville Colonels | 4 | May 5 | May 10 | 3.8 runs | |
| Pittsburgh Pirates | 4 | Jun 5 | Jun 8 | 5.8 runs | |
| Pittsburgh Pirates | 4 | May 9 | May 12 | 3.5 runs | |
| St. Louis Perfectos | 4 | Oct 2 | Oct 5 | 2.8 runs | |
| St. Louis Perfectos | 4 | Jun 23 | Jun 25 | 2.5 runs | |
| Washington Senators | 4 | Sep 2 | Sep 5 | 11.8 runs | |
| Washington Senators | 4 | Aug 22 | Aug 27 | 8.0 runs | |
| Washington Senators | 4 | Aug 1 | Aug 7 | 3.5 runs |
Yes, multiple losing streaks during the 1899 MLB season are in the all time top 50 losing streaks in the same season. The 24 game losing streak by the Cleveland Spiders was the 1st longest same season losing streak in MLB history. The 16 game losing streak by the Cleveland Spiders was the 26th longest. The 14 game losing streak by the Cleveland Spiders was the 45th longest.
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