1899 Cleveland Spiders
The story of the Spiders is almost too strange to be true. After the 1898 campaign, Cleveland owners Frank and Stanley Robison purchased the ailing St. Louis Browns' club, which had finished at 39-111. The Robisons raided the roster and moved the club to Cleveland to play as the Spiders. The incumbent Cleveland squad, which had posted a respectable 81-68 record, was moved to St. Louis and rechristened the Perfectos. With a handful of players obtained from the Browns, the Perfectos ended up tied for fifth place with a 84-67 mark. The Spiders became one of the worst teams in major league history, winning just 20 games all year and compiling a 24 game losing streak from August 26th to September 16th. This club was so bad, they were forced to play most of their games on the road since virtually no one would pay to see them at home. The story is recounted in its entirety in my book Cellar Dwellers.
By the time the '61 campaign rolled around, the Phillies were still looking for their first World Series victory and had been to the October showcase just twice. From July 29th to August 30th, they assembled a 23 game losing streak--the second longest in major league history. After going 15-47 in July/ August, they improved moderately, posting a 10-14 record in September. None of the Philly regulars compiled a batting average above the .300 mark and only one player, utility man Don Demeter, reached the 20-homer threshold. Hall of Fame pitcher Robin Roberts--a once dominant presence on the hill--was in serious decline that year, suffering through the worst season of his career with a 1-10 record and a 5.85 ERA.
Neither of the Ripkens (Cal Jr. and Billy) could save their father's managerial job in '88 as the O's got off to an 0-6 start. Cal Sr. was dismissed and replaced with Frank Robinson, who could not stop the team from rattling off an impressive string of 21straight losses to start the season.The club finished in last place with a 54-107 record, but played decent ball in August, compiling a 14-15 mark. Ripken Jr. and Eddie Murray both had respectable seasons offensively, but Baltimore pitchers were far too generous with 3 of 4 members of the starting rotation averaging more than 4 runs per 9 frames. The O's bounced back with Robinson at the helm, fisishing second in the AL East during the '89 campaign with a 87-75 mark.
1916 Philadelphia A's
After suffering a 1914 Series sweep at the hands of the Braves, Connie Mack sold off most of his best players, including Hall of Fame infielders Eddie Collins and Frank "Home Run" Baker. The results were disastrous as the A's posted a 36-117 mark in 1916, stringing together 20 straight losses from July 21st to August 8th. In June/ July, the club was 5-47 overall. At 41 years of age, Hall of Fame infielder Napolean Lajoie did very little to help the A's, compiling the lowest batting average of his career at .246. The pitching staff was a mess and Mack auditioned more than 20 players on the mound that year--many of them college players.
While the expansion Mets were claiming the first world championship in franchise history, the fledgling Expos were making an inauspicious debut with a deplorable 52-110 record. This included a string of 20 straight losses from May 13th to June 7th. Still, the club generated a bit of fan interest, drawing more than a million fans to Jerry Parc and finishing with a rank of #7 (of 12) in regard to attendance. Outfielders Rusty Staub and Mack Jones generated most of the offensive punch with 51 homers and 158 ribbies between them. There were no other glaring bright spots with the exception of manager Gene Mauch, who remained at the helm the following year and turned the club around (to an extent). The Expos won 73 games in 1970 and flirted with the .500 mark every year from '73-'75 under Mauch's watch.