 Chalobah scored his first Forest goal in a 3–1 defeat away to Yeovil Town on 26 October 2013.On 16 January 2014, Chalobah joined Middlesbrough on loan for the remainder of the 2013–14 season.On 25 January 2014, Chalobah made his debut against Leicester City, coming off the bench in the 77th minute to replace Emmanuel Ledesma.