 Eastleigh managed to get to the semi finals of the National League play-offs with Southwood playing a key part in that, also getting player of the month in April.On 1 August 2019, Southwood joined Hamilton Academical on loan until 5 January 2020.On 21 January 2020, Southwood signed a new contract with Reading until the summer of 2021, and then returned to Hamilton Academical on loan until the end of the season.