Dolan's request was approved by the Vatican five weeks after his letter, according to the files. The church was facing hundreds of lawsuits over alleged child molestation at the time.
The released documents include extracts from the personnel files of 42 members of the Milwaukee clergy against whom there were "substantiated" allegations of sexual abuse going back 80 years. Lawyers for the alleged victims accused Dolan of helping the archdiocese to carry out fraud by filing for bankruptcy after moving the money to the cemetery fund.
"These documents show that if they want to move money to protect it from survivors they can act quick as a fox," said Jeff Anderson, one of the lawyers.
A spokesman for Dolan described the disclosures as "old and discredited attacks".
The spokesman said the documents showed that bishops had kept promises such as "permanent removal from ministry of any priest who abused a minor; complete co-operation with law enforcement officials".
However, the letter threatens to challenge the reputation of the cardinal, who earned praise from within the church for his handling of the Milwaukee scandal after being appointed to resolve it.
Supporters pointed to other documents in the released files that showed that in 2003, the cardinal pleaded with the Vatican to defrock a priest who had been accused of repeatedly abusing children.
"Our new-found awareness of the severity of damage caused by sexual abuse at the hands of clergy makes it impossible for us to ignore this situation."
However, documents also showed that the Milwaukee archdiocese paid off paedophile priests with tens of thousands of dollars or transferred them elsewhere instead of removing them from the church.