The actual answer to this question is shrouded in history. But the BIKE Athletic Company based in Knoxville, TN has stated in its athletic supporter products in recent years that it invented the athletic supporter as we know it in 1874. So I would think that athletes would have begun wearing jockstraps for sports in the late decades of the nineteenth century. I have a book in my personal library entitled: Baseball Archaeology: Artifacts from the Great American Pastime (San Francisco, Chronicle Books, 1993). On pages 38-39 is the first known "Safety Cup" worn by catcher Claude Berry in 1916. I believe this steel athletic cup is enshrined in the Baseball Museum in Cooperstown, NY. One would have to research past editions of the Rules for Major League Baseball for mandatory use of jocks and cups by players for a more accurate clue for this question. Athletic supporters and cups have evolved in sophistication and comfort over the years. Most cups worn by baseball players these days are of the banana cup variety, of which the Original Banana Cup, the BIKE CUP, and the XO Pro Cup are the best examples.
A boy should wear a jock/cup for little league and continue through his life playing sports. As a boy grows and matures like from grades 5 and up a regular jockstrap should be introduced as the Best thing to protect his family jewels. As boys are growing by age 12 if they start wearing boxers a simple swimmer jock should be worn daily under their boxers for support. eg.. Bike swimmer jock or Bike reg straps work great.
According to Wikipedia, "The earliest known reference to baseball is in a 1744 British publication, A Little Pretty Pocket-Book" whilst American Football can be traced back to the mid 19th Century (1850-ish) as an evolution if association football (soccer) and rugby.As far as professional baseball and football go, professional baseball traces back to the 1850s played by organised baseball clubs, whilst wikipedia has this to say on professional football: "origin of professional football can be traced back to 1892, with William "Pudge" Heffelfinger's $500 contract to play in a game for the Allegheny Athletic Association against the Pittsburgh Athletic Club. The first Professional "league" was the Ohio League, formed in 1903, and the first Professional Football championship game was between the Buffalo Prospects and the Canton Bulldogs in 1919."
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