The 1944 World Series was an all-St. Louis World Series, matching up the St. Louis Cardinals and St. Louis Browns at Sportsman's Park. It marked only the third time in World Series history in which both teams had the same home field (the other two being the 1921 and 1922 World Series in the Polo Grounds in New York City).

1944 saw perhaps the nadir of 20th-century baseball, as the long-moribund St. Louis Browns won their only American League pennant. The pool of talent was depleted by the draft to the point that in 1945 (but not 1944), as the military scraped deeper and deeper into the ranks of the possibly eligible, the Browns actually used a one-armed player, Pete Gray. Some of the players were 4-Fs, rejected by the military due to physical defects or limitations which precluded duty in the trenches. Others divided their time between factory work in defense industries and baseball, some being able to play ball only on weekends. Some players avoided the draft by chance, despite being physically able to serve. Stan Musial of the Cardinals was one. Musial, enlisting in early 1945, missed one season. He rejoined the Cardinals in 1946.

The Chronicle-Telegraph Cup was the trophy awarded to the winner of a postseason competition in American professional baseball in 1900. The series, played only once, was a precursor to the current World Series.

The Pittsburg Pirates finished in second place, 4.5 games behind the Brooklyn Superbas in the 1900 National League (the only Major League in American baseball at the time). Fans of the Pittsburgh club felt their club was every bit the equal of the Brooklyn nine. While Brooklyn led the league in offense, Pirates rooters claimed their team, which led the NL in strikeouts with the league-best ERA, boasted the pitching to best Brooklyn. A local newspaper, the Pittsburgh Chronicle Telegraph, offered to award a silver cup to the winner of a best-of-five series between the two teams.

Despite the series being held in Allegheny, Pennsylvania, which became annexed into Pittsburgh in 1907, the Superbas prevailed, 3–1. The teams were evenly matched in most statistical categories — both totalled 15 runs apiece, batted about .230 and had comparable numbers of extra-base hits (neither team hit any home runs) and walks. Both teams' ERAs were below 1.30.

The 1972 World Series matched the American League champion Oakland Athletics against the National League champion Cincinnati Reds, with the Athletics winning in seven games. These two teams would meet again in the fall classic 18 years later in 1990. Their managers would meet again in the fall classic a dozen years later in 1984, managing different teams and swapping leagues.

Background

The A's won the American League West division by 5 ¹⁄₂ games over the Chicago White Sox, then defeated the Detroit Tigers three games to two in the American League Championship Series. The Cincinnati Reds won the National League West division by 10 ¹⁄₂ games over both the Los Angeles Dodgers and the Houston Astros. The Reds defeated the Pittsburgh Pirates three games to two in the National League Championship Series, marking the first year in which an LCS series in either league went the full five games since divisional play was introduced in 1969. The Reds, who won one fewer game than the Pirates during the regular season, became the first team in MLB history to reach the World Series without having the best record in its respective league. In each of the first six League Championship Series, the team with the better record advanced to the World Series.