The comments come from "Trumped!" a syndicated radio feature that aired from 2004 to 2008, which was recently rediscovered by the Wall Street Journal
"Hillary Clinton said she'd consider naming Barack Obama as her vice president when she gets the nomination, but she's nowhere near a shoo-in," Trump said in 2008. "For his part, Obama said he's just focused on winning the nomination although at least one member on his team said Clinton would make a good vice president. Well, I know her and she'd make a good president or good vice president."
The series featured about one minute of daily commentary from Trump, often speaking over "For the Love of Money," the theme song to his "Apprentice" reality show. There are about 1,000 episodes of the Premiere Networks syndicated show, according to the Journal.
"A lot of people think a Clinton-Obama or Obama-Clinton pairing would be a dream ticket in November, but for that to happen one of them has to be willing to serve as number two. Until that time, it's going to be very interesting," Trump added in his 2008 comments.
CNN has reached out to the Trump campaign for comment on the recordings.
This is not the only time that Trump praised Clinton during her 2008 run. He told CNN's Wolf Blitzer in 2007 that Clinton is "very talented" and wrongly predicted that she'd be the Democratic nominee.
"I think she will be," he said on CNN's "Situation Room." "I know her she very well. She's very talented. And she has a husband that I also like very much. I think she's going to get the nomination rather easily."
Trump went on to call Clinton "terrific."
"If it is Hillary Clinton vs. Rudy Giuliani for president of the United States ... where does Donald Trump stand," Blitzer asked.
"I can tell you this. They're both terrific people, and I hope they both get the nomination," Trump replied. "And then it's going to be a very interesting race. And I always go with one person. I will make a decision."
Trump has donated to Clinton in the past and even invited her and Bill Clinton to his wedding. But his 2008 commentary strikes a significantly different tone from his assessment of Clinton in 2016.
"Crooked Hillary Clinton is the secretary of the status quo and wherever Hillary Clinton goes, corruption and scandal will follow. Just look at her life," he said Monday.
In the recordings, Trump also expressed a stronger position on gun control than what he's advocated for in 2016. The guns rights advocate opposed a decision to allow hunting-education classes in West Virginia schools calling it in 2008 "a dangerous risk."
"We hear way too many stories about school violence, so the thought of voluntarily putting guns in the classroom seems like a really bad plan," he said on the recording.
But in 2016, Trump has advocated for more guns in the classroom in response to school shootings. Trump told CNN in May that "school resource officers" or trained teachers should be the ones carrying guns.
He stood by his adamant criticism of gun-free zones but backed away from his blanket call to eliminate all gun-free zones in schools, saying they would only be eliminated "in some cases."
"I don't want to have guns in classrooms, although in some cases teachers should have guns in classrooms, frankly," he told Fox News in May.