In a court filing, US attorneys say the checks are further evidence that the Wall Street broker planned to keep his assets out of the hands of investors, the BBC reports.
Mr Madoff has previously been accused of mailing more than $1 million in jewelry and other valuables to relatives to prevent them from being seized by investigators looking into his alleged $50 billion fraud.
He is also said to have planned to distribute more than $200 million in cash to close friends and family once the scheme, which Mr Madoff apparently described as "basically, a giant Ponzi scheme", eventually collapsed under its own weight.
Prosecutors want Mr Madoff jailed until his trial for securities fraud.
However, the broker's lawyers say he poses no threat or flight risk and should remain on his $10 million bail. Mr Madoff is currently under house arrest at his Manhattan apartment.
In related news, investigators in the UK and France have begun their own inquiries into Mr Madoff's business operations in their respective countries.