Australian midfielder Massimo returned to Town in January of 2023, having previously spent a spell on loan at Portman Road from Tottenham Hotspur in 2012. 

After coming into the side in February of 2023, Massimo played a vital role in Town’s surge to promotion, during a run where he didn’t finish on the losing side in any of his 15 League One appearances. He scored two goals, notably netting the second goal in the 6-0 victory over Exeter which ultimately secured promotion. 

Massimo signed a new one-year contract with the Club following promotion, having joined from Middlesbrough, where he had spent the first half of the 2022/23 season after a three-year spell with Sheffield Wednesday. 

Prior to that, the midfielder had been a regular in the Championship with Queens Park Rangers, following two seasons at Swindon Town, initially on loan from Spurs before making his move to Wiltshire permanent. 

He has won nearly 50 caps for his country and was named player of the tournament at the 2015 Asian Cup, while also being part of the Socceroos’ squads for the 2014 and 2018 FIFA World Cups.