On November 7, 2018, Whitehead was claimed off waivers by the [[Cleveland Browns]].<ref>{{Cite web |date=November 7, 2018 |title=Browns claim DBs Phillip Gaines, Jermaine Whitehead |url=https://www.clevelandbrowns.com/news/browns-claim-dbs-phillip-gaines-jermaine-whitehead |website=ClevelandBrowns.com}}</ref> On September 29, 2019, he had his first NFL career [[interception]] and forced [[fumble]] in a game against the Baltimore Ravens.<ref>{{Cite news |last=Kerr |first=Jeff |date=September 29, 2019 |title=Browns at Ravens final score: Nick Chubb goes for three touchdowns as Cleveland takes over first place in AFC North |work=CBS Sports |url=https://www.cbssports.com/nfl/news/browns-at-ravens-final-score-nick-chubb-goes-for-three-touchdowns-as-cleveland-takes-over-first-place-in-afc-north/ |access-date=September 29, 2019}}</ref> Whitehead was waived on November 4, 2019 after posting "several threatening and racist messages for people who criticized him" following the team's loss to the Denver Broncos, a game in which he missed a number of crucial tackles.<ref>{{Cite web |last=Patra |first=Kevin |date=November 4, 2019 |title=Browns cut safety Whitehead after social media posts |url=http://www.nfl.com/news/story/0ap3000001073390/article/browns-cut-jermaine-whitehead-after-social-media-posts |access-date=November 4, 2019 |website=NFL.com |language=en}}</ref> Whitehead later apologized for the messages.<ref>{{Cite web |last=Gaydos |first=Ryan |date=November 6, 2019 |title=Ex-Browns defensive back Jermaine Whitehead apologizes for threatening critics on social media |url=https://www.foxnews.com/sports/browns-jermaine-whitehead-apologizes-threats-social-media |access-date=November 7, 2019 |website=[[Fox News]]}}</ref>
