Bringing the curtain down on an active weekend of tweeting, during which he addressed suggestions of collusion with Russia and criticised the FBI, the President declared he had been left unimpressed by the talk show host’s appearance on CBS News programme 60 Minutes.
Oprah met 14 voters in Michigan last year – seven who voted for Mr Trump and seven who did not – to discuss how they felt about the President, and they reconvened to mark his first year in office.
It was broadcast on Sunday night and Mr Trump tuned in.
“Just watched a very insecure Oprah Winfrey, who at one point I knew very well, interview a panel of people on 60 Minutes,” he tweeted.
“The questions were biased and slanted, the facts incorrect.
Hope Oprah runs so she can be exposed and defeated just like all of the others!”
Points of discussion on the show included the President’s new tax laws, his “s***hole countries” comment, policies on Islamic State and North Korea, and being safe in the knowledge that it was now OK to wish people a Merry Christmas.
Oprah – who sparked speculation about a presidential bid in the wake of her famed Golden Globes speech – questioned whether Mr Trump was held to a different standard regarding sexual harassment, and his impact on the global perception of the US.
The 63-year-old also asked whether people felt safer than they did under former US president Barack Obama, which – like all of her questions – generated a mixed response.
The programme and Mr Trump’s subsequent tweet sparked renewed calls on social media for Oprah to run for the Democrats in 2020, despite her previously ruling it out.
Responding to the rumours earlier this year, Mr Trump said he did not think Oprah would run, and that he would secure another four years in office if she did enter the race.