Bale caught the world's attention in October 2010 when he scored a hat-trick at the San Siro and then went on to make a mockery of Brazil right-back Maicon when Inter went down 3-1 to Spurs in the reverse fixture the following month.
The victory, and the "Taxi for Maicon" chants that rang out around White Hart Lane that night will live long in the memory of Tottenham fans, but Bale's determination not to dine out on those two games for the rest of his career has allowed him to develop in to an even more devastating player.
Bale starred for Tottenham last season, but it is only in this campaign that the 23-year-old has come to be regarded as having similar quality to the likes of Cristiano Ronaldo and Lionel Messi.
Bale has scored 20 goals for Spurs this season - comfortably his best return as a professional - and his manager thinks the Welshman is primed to cause yet more damage to Inter when the two teams lock horns in the first leg of their Europa League last-16 tie at White Hart Lane Thursday.
"I think Gareth has evolved as player. He is even more threatening now," the Tottenham manager told a press conference.
"I remember seeing the highlights of Inter - Tottenham, and how Tottenham came back into the game late on.
"Maicon was an outstanding right-back, one of the Brazilian right backs, so to see a young player like Gareth play like he did against him demonstrates his talent.
"Now, two years on, he plays in a different position. He's become a different player; a bigger player and a more complete player.
"He's the kind of player who can determine the outcome of a game, as we've seen in recent matches."
Bale, as Villas-Boas points out, has been crucial to the unbeaten 12-match run that has seen Spurs climb above Chelsea in to third place.
The Welshman has scored nine times in seven games. Without those goals Tottenham would be seventh.
Bale has struggled with injuries in the past, but Villas-Boas sees no reason to rest the forward.
"He is fine. Most of the players feel fine and fresh," the Portuguese said.
"There is a lot of rest time between a Thursday and a Sunday (when Spurs play Liverpool."
Bale has been linked with a move to Real Madrid thanks to his exploits this year.
The suggestion he could be bound for the Spanish capital gathered pace yesterday when he was spotted at their Champions League clash against Manchester United, but Villas-Boas denied anything should be made of Bale's attendance.
"I had no problem with it," the 35-year-old said.
"I was told about it in the afternoon. We spoke about the game (today). It's a great game of football."
While much of the attention will understandably be on Bale tomorrow, the visit of Inter also brings back fond memories for Tottenham's manager.
Villas-Boas spent 18 months at the San Siro operating as Inter's head scout under Jose Mourinho before he decided to go it alone after being offered the manager's position at Academica de Coimbra.
Villas-Boas' decision to leave his mentor and branch out in to management angered the now Real Madrid boss at the time, but his protege still thinks he made the right choice.
"It was a difficult moment of my professional life (to leave Inter)," Villas-Boas said.
"At that time I was scouting for Jose. We had conversations because I wanted to be a little bit more involved with first-team training
"Jose had always seen me doing the job I was doing.
"It was a difficult step to take, but it was probably the right one."
Villas-Boas confirmed today that striker Emmanuel Adebayor has only a slim chance of playing due to a knee injury he suffered in Sunday's north London derby win.
Villas-Boas is likely rotate his goalkeepers again, with Hugo Lloris making way for Brad Friedel.