The 22-year-old left-back will come under the microscope once again in the Midlands after failed moves to the south coast and Sheffield Wednesday.
Masampu had an opportunity to impress Blues boss Danny Cowley while on trial at Fratton Park in summer, but the former Lincolnn boss decided to explore other options for the position.
This saw Conor Ogilvie arrive from Gillingham and Liam Vincent sign from Bromley as the pair were selected to provide the competition needed for Lee Brown.
Prior to his spell in PO4, the defender was picked up by former Pompey man Darren Moore at Hillsborough but, again, failed to impress significantly enough to receive a contract in Yorkshire.
And he’ll be hoping it’s third time lucky as he looks to break back into professional football.
Before his League One trial periods, Masampu was last seen playing for Whyteleafe and Dulwich Hamlet following his release from Chelsea in 2019.