The young midfielder's parents, Mario and Ira, travelled all the way from Australia to watch him play live for the first time in England.
Based in Massimo's home town of Sydney, Mario and Ira touched down at Heathrow at 6am and took their place at the County Ground for Swindon's League One encounter against Stevenage Borough.
Massimo, one of four Spurs players on loan at the Robins, responded with man-of-the-match display including a magnificent winning goal, a bullet-like strike from 25 yards, as Swindon secured a 1-0 victory.
"It was a big day," said Massimo, who joined us in January, 2011. "My parents haven’t seen me play in England, they haven’t been over so for them to be there and me to score the winning goal was something special. It made my day."
Grant Hall also played although Ryan Mason and Alex Pritchard missed out through injury.
"Everyone has settled in and we're all enjoying it," added Massimo. "The fact we all know each other really takes the pressure off. We all help each other out."