Mr Corbyn, who now sits as an independent MP, tweeted his support for Kareem Dennis, better known as Lowkey, at the weekend.
It came as the hip-hop artist penned a tweet about his four-city concert tour of the Netherlands.
Sharing footage from the tour, he wrote: "A beautiful conclusion to 4 city tour of the Netherlands in Amsterdam last night. Thank you to all who came out!"
In response, Mr Corbyn wrote: “Well done Lowkey, what energy and good messages you carry!”
Songs performed by Lowkey this year include Long Live Palestine, featuring the lyrics “nothing is more antisemitic than Zionism” and “Israel is a terror state, they’re terrorists that terrorise”.
Jeremy Corbyn's tweet, addressed to Lowkey Twitter/Jeremy Corbyn
He references the "Zionist lobby" in other tracks from his setlist and has previously labelled Israel a "racist endeavour".
Earlier this year, the National Union of Students invited Lowkey to perform at a conference for students from marginalised groups.
But Lowkey pulled out following concerns raised by Jewish students who accused the rapper of antisemitism.
And the NUS was heavily criticised for telling Jewish students to "go into an existing safe space” during the live performance before it was scrapped.
Lowkey is a supporter of Mr Corbyn, releasing a “Vote Corbyn” rap video on the eve of the 2019 general election.
A spokesman for the Campaign Against Antisemitism (CAA) told the Telegraph: “Whether despite or because of this inflammatory record, Lowkey has drawn praise from none other than Jeremy Corbyn for the ‘good messages you carry’.
“Yet still, the Labour Party is happy to have Mr Corbyn as a member. Why is the Party so stubbornly unable to see what all of the rest of us can?”