That's the prize waiting for the winners of the play-off semi-finals between the Robins and Brentford and Sheffield United and Yeovil.
Massimo and Spurs team-mate Nathan Byrne have nailed down regular places in the Swindon team since joining them on loan in March.
They finished sixth in League One while Brentford had the heartbreak of missing automatic promotion to the Championship in such dramatic circumstances against Doncaster last weekend.
They meet at Swindon's County Ground on Saturday before the return at Griffin Park on Monday.
"The Wembley part of it hasn’t really hit me yet," said Massimo. "The first leg is on a Saturday and I’m just treating it as another game and at the moment I’m just concerned about playing well.
"I’m on loan, proving myself and this is where you can show people what you can do. These are the most pressured games. If we get to Wembley, we’ve achieved that, but the pressure is then on again to try and win."
Massimo, who captained our Under-21s and played 13 times in the Barclays U21 Premier League before switching to the Robins, has quickly adapted to life as a central midfielder in League One.
However, as he admits, it's not easy. "People think because we’re going down to League One and we belong to a Premier League club that it’s easier, but my debut against Doncaster was the toughest game I’ve experienced. It was so physical. I’m used to that, enjoy it and it’s about adapting.
"I haven't played them yet, but people say Brentford are the best team. I've watched them, and that's probably right, but it all comes down to the day in these play-offs."