In a video unearthed by NY magazine, Matthews can be seen making a few inappropriate - and sexist - jokes about then-Democratic presidential candidate Hillary Clinton ahead of a January 5, 2016, interview.
In a statement, Matthews offered a mea culpa for the remark.
A spokesperson for Clinton did not immediately respond to a request for comment, but aides to the former Democratic presidential candidate expressed revulsion and bewilderment over the footage. "As I recall he got pretty angry with her after she challenged him during foreign policy section", Palmieri tweeted.
The website also listed some of Matthews' controversial remarks about Clinton, some of which were made on air.
Back in 2008, he also pinched Clinton's cheek after conducting an interview with her, saying afterwards that he was "not obsessed" with the former First Lady. Matthews said to a crew member. "We keep forgetting it".
Still, Matthews has long shown that he has no love for Clinton.
"Did you see her walk?" MSNBC later confirmed the report from The Daily Caller that Mathews was formally reprimanded and that the employee had been paid compensation upon leaving her job. "My God is that good".
MSNBC said it made a separation-related payment to an assistant producer on "Hardball" after she made a sexual harassment claim in 1999.