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Stubblefield's name and those of several of his Oakland Raiders team members were found on the list of clients of the Bay Area Laboratory Co-operative that had given performance-enhancing drugs to Marion Jones and others. Although initially he lied to federal investigators about using both EPO and THG, after he was charged on January 18, 2008, Stubblefield cooperated with both federal and NFL investigators and turned over the names of players, agents, and trainers that he suspected of using drugs.^[4]

Because of his cooperation with the investigation, he received a fairly light sentence after pleading guilty to lying to federal investigators on February 6, 2009. He served two years' probation.^[5]

On December 9, 2010, San Francisco U.S. District Court judge Susan Illston sentenced Stubblefield to 90 days in jail for stealing his ex-girlfriend's mail by way of fraudulent submission of a change-of-address form.^[8]

On May 2, 2016, he was charged with sexually assaulting a disabled woman, who at the time of the incident was 31 years old. The incident occurred April 9, 2015. Stubblefield originally contacted her through a babysitter website.^[9] On July 27, 2020, Stubblefield was convicted of rape and on October 22, 2020, was sentenced to 15 years to life in prison.^[10] In December 2024, a court overturned Stubblefield's conviction on appeal, as the prosecution was found to be in violation of the California Racial Justice Act of 2020, which forbids racially biased language and rhetoric from cases made by prosecutors.^[11]