Experts say the material may offer more insight about the White Sox, whose alleged notorious actions during the series against the Cincinnati Reds has become one of the darkest events in baseball history.
"This could be a treasure trove," baseball author Gene Carney said.
It is unclear exactly how the documents, whose existence was previously unknown, ended up together or where they have been over the past eight decades. Mastro Auctions in Burr Ridge declined to reveal the identity of the two sellers and said they most likely purchased the box without knowing exactly what was inside.
The papers, examined by the Chicago Tribune, appear to contain documents from the 1921 criminal trial against eight White Sox players accused of throwing the 1919 World Series as part of a gambling scandal. The papers also include documents from a 1924 lawsuit in which some of the players sued the Chicago franchise for back pay.
The White Sox players, including "Shoeless" Joe Jackson, were acquitted, but all were permanently banned from the game by the first commissioner of baseball.
The Baseball Hall of Fame and Museum will receive photocopies of the documents, officials said.
"We don't know what's out there," said Jim Gates, director of the Baseball Hall of Fame Library. "We don't know what's missing, what's lying around."
A White Sox spokesman said the franchise is also interested in seeing the documents.
The documents appear to contain hostile correspondence between then-White Sox owner Charles Comiskey and then-American League president Byron Johnson. The box of documents also shows two cashed checks, which were likely exhibits from the civil trial over back pay.
There is also a 1920 letter purportedly from Comiskey to a fan, which appears to have been written just after news of the scandal became public.
"Words utterly fail to express my appreciation of the kind things you and my other friends have taken every opportunity to express," the letter reads. "They are indeed compensation for much that I have recently endured."
The documents will be up for auction until Dec. 13.