It’s been fifteen years since Major League Baseball instituted Interleague Play and the game has been better for it. Midseason attendance spikes. It drives revenue and frankly, especially in the case of regional rivalries, a little healthy competition between family members is never bad.
In Chicago, it’s the “Crosstown Classic”. In northern California, it’s the “Bay Bridge Series”. However, the most famous of these regional rivals would easily have to be New York’s very own “Subway Series.”
Before Interleague Play was a gleam in Bud Selig’s eye, the “Subway Series” was pretty common in New York. After all, two New York teams have faced each other in the World Series fourteen times dating back to 1921. (Technically two New York teams played each other in the “World Championship Series” in 1889, but being that the Subway didn’t make its debut until 1904, that series could probably best be described as a “Trolley Series.”) The most of the regional rivals by far.
Beyond the postseason, the Yankees and Giants used to play exhibition series against each other from time to time. These match-ups were known as the "City Series." Sometimes they were even played in October, on the rare occasion that either team wasn’t in the World Series. After 1940, this became difficult because the Yankees routinely appeared in the World Series. In the seventeen-year span between 1941 and 1957 (when the Giants and Dodgers left for California), the Yankees appeared in the World Series twelve times. They only failed to reach the Series in 1944, 1945, 1946, 1948 and 1954.
Prior to the abandonment of New York by the city's two National League teams, the Yankees and Dodgers began to play an annual midseason exhibition game called the Mayor's Trophy Game. It benefited sandlot baseball in New York City. The proceeds raised by the Yankees went to leagues in Manhattan and the Bronx while the proceeds raised by the Dodgers went to leagues on Long Island and Staten Island.
Interest in the annual charity event was revived in 1963 with the expansion New York Mets. With it, bragging rights to the city were back on the line. The Yankees were no longer the only team in town and at some points they weren’t even the best team in town. (For those of you born after 1996, this seems like an impossible idea, I know.)
Most of the time, these games weren’t very competitive. If one team was great, the other was usually very bad. After dwindling interest as well as public bickering between the owners of both teams, the Mayor's Trophy Game was discontinued following the 1983 season.
It was revived again as a pre-Opening Day series titled the "Mayor's Challenge" and hosted many recent Yankees’ and Mets’ Greats like Doc Gooden, David Cone, Al Leiter and Don Mattingly. However, as the Major League schedule evolved and the game became harder to schedule, it was eventually discontinued for good in 1992.