Simpson, convicted in 2008 of storming a Las Vegas hotel room with other men and taking thousands of dollars worth of memorabilia he said dated from his sports career, is seeking parole for convictions on robbery, kidnapping and burglary charges.
Simpson, 66, is serving consecutive sentences and would still need to finish his sentences for assault with a deadly weapon and other charges related to the 2007 incident.
The Pro Football Hall of Fame running back was dressed in prison denim when he appeared via video conference on Thursday from Lovelock Correctional Center and spoke to a parole board commissioner in Carson City.
A sombre-looking Simpson said the sports collectors he took property from "could have it all" if he could "get these five years back" that he spent in prison.
"I missed my two younger kids, for the most part, getting through high school," Simpson said. He added that he also was unable to attend his sister's funeral.
In 1995, Simpson was acquitted in California of two counts of murder in the stabbing and slashing deaths of his ex-wife Nicole Brown Simpson, and her friend Ronald Goldman. He later lost a wrongful death case brought by Goldman's family.
Even if Simpson were successful in this and future parole requests, he would not be released from prison before 2017, said David Smith, a spokesman for the Nevada Board of Parole Commissioners.
The Nevada parole board will likely rule next week on Simpson's request, Smith said.
"He's been a model inmate, so we don't expect him to have any problems making parole," said Simpson's attorney, Patricia Palm, who is representing him in his request for a new trial on the charges.
Simpson told the parole commissioner he was only trying to retrieve property that he believed belonged to him.
He is eligible for parole on his convictions for robbery, kidnapping and burglary, but not assault with a deadly weapon, Smith said.
Simpson, who has gained weight and seen his hair recede and turn greyer while behind bars, said he has mentored young inmates and that he performs custodial duties in the gym at his prison in remote northeast Nevada.
Because of credits for good behaviour, Simpson would likely serve a total of no more than about 20 years in prison even if he were never granted parole, said Clark County Chief Deputy District Attorney Leon Simon, who is involved in fighting Simpson's request for a new trial.
In May, Simpson requested a new trial on the grounds that his former attorney, Yale Galanter, mishandled the 2008 case and had a conflict of interest because he knew in advance that the former athlete planned to confront the sports dealers.
A Clark County judge is expected to rule within weeks on Simpson's request for a new trial.