The Portuguese has lamented the fact his side travel to Villa Park for their third game in six days following a 3-0 UEFA Europa League win over Tromso and a 1-0 victory against Cardiff City in the Premier League on Sunday.
Prior to those confidence-boosting wins, the latter of which was sealed with a stoppage-time goal, Villas-Boas claimed that the hectic schedule is asking too much of his players and could prove to be dangerous.
"How can a game be scheduled after two days, immediately putting careers at risk with injuries?" he said.
"I find it absolutely incredible that we have to risk injuries to our players in a game that they play on that Tuesday. The problem is that it puts the players in a very difficult situation.
"It's also nothing new in English football. I had the same thing once with Wolverhampton (Wanderers) and Chelsea, when I was at Chelsea, and I spoke the same way."
The game will represent Spurs’ first involvement in this year’s competition due to their European commitments, but Villas-Boas expressed his concerns over the welfare of his squad.
"The second day of recovery is the most dangerous day for a player to pick up an injury," he said.
"If this is not taken into account I think it's bad. Other things have to be respected - televised games, fixture organisation, the police - comes into account because of the fixtures that are being played on the Tuesday and Wednesday.
"But the problem is that in the end Tottenham was chosen to play on Tuesday, with only the Monday to recover from the last match, and that puts us in a very difficult position."
Villa, semi-finalists in last year’s competition, booked their place in the third round with a comfortable 3-0 home win over League One side Rotherham United.
Manager Paul Lambert is wary of the threat that Tottenham will pose.
"Any cup game you get, you want to be at home," he said.
"But we're up against a top, top side. Andre has some top players but that's what you have to come up against.
"It will be a great game. I am pretty sure the stadium will be full or not far off it."
Tottenham won 4-0 on their previous visit to Villa Park back in December and you have to go back to January 2008 for the last time they were defeated at the Midlands ground.
