The Irish livewire enjoyed his first foray into Premiership football with the Sky Blues under the management of Gordon Strachan after he left Wolves in August 1999.
He was a firm favourite with the crowd and instantly made his mark on the top flight. Now, three clubs later, he heads back in Tottenham colours but says his second club remains close to his heart.
"It is going to be special as I have great memories from Highfield Road," said Robbie on Tuesday. "I was there with Gordon Strachan and had a great season there.
"Coventry are very close to my heart and the fans, from day one, were brilliant to me. It is always nice to go back and hopefully I'll get a good reception.
"I really enjoyed it, taking a step up to the Premiership was always going to be hard, but I had good players around me and a good manager who helped me in every possible way - I loved every minute of it."
And it certainly took a pretty big move to tempt him away from Coventry at the time...
"It took Inter Milan! It was good though and I'm really looking forward to it. I haven't been back to Coventry or Wolves yet in a competitive game and I can't wait for it."
A teammate of Robbie during his year at Coventry now happens to be manager of the club and Robbie says he long suspected Gary McAllister would end up in charge.
"I got on very well with Macca and still speak to him every now and again. He is a good bloke and I knew when I was at Coventry that he was always going to become manager.
"He is just one of those people who knows the game inside-out and is very clever on the pitch. I'm sure he will prove to be the same off the pitch too. I've got a lot of respect for Gary."
Robbie Keane makes a first return to Coventry City as a player tonight and he hopes it will be a special occasion.