On June 19th, 1846, the first organized baseball game played under Alexander Cartwright's newly codified rules took place at Elysian Fields in Hoboken, New Jersey, and it was an absolute disaster for one team in particular. The New York Nine demolished the Knickerbockers by a score of 23 to 1 in just four innings.
Now here's where it gets deliciously ironic. Alexander Cartwright himself was a member of the Knickerbockers team, meaning the man who literally wrote the rulebook got thoroughly trounced in the first official game played by those very rules. Imagine spending months carefully crafting the regulations for a new sport, publishing them with great fanfare, and then your team proceeds to get utterly humiliated in the inaugural match.
The game took place on a pleasant summer day, and Cartwright had established rules that are remarkably familiar to modern baseball fans, including the diamond-shaped infield, foul lines, three strikes for an out, and three outs per inning. What he apparently hadn't established was a competitive team capable of implementing these rules effectively.
The Knickerbockers were actually a social club of prosperous New York gentlemen who enjoyed recreational activity, while the New York Nine were simply better players. Adding insult to injury, Cartwright served as the umpire for this game as well, so he had to officiate his own team's catastrophic defeat while enforcing the rules he'd invented.
The losing team reportedly had to pay for dinner and drinks afterward, which was customary for the era. One can only imagine the atmosphere at that particular meal.