Tottenham play Aston Villa in the third round of the Capital One Cup on Tuesday, just two days after the north London club play at Cardiff in the Barclays Premier League.
Given that Spurs play Tromso in the Europa League on Thursday, Villas-Boas' squad face a hectic period of three games in six days.
The Portuguese understands the need to schedule the Cardiff game on Sunday, but he is perplexed as to why his squad will have to play at Villa Park 48 hours later, especially when some Capital One Cup fixtures are taking place on Wednesday.
"After this (Europa League) game, we have not only the Sunday game but the Tuesday game, which I found as an incredible surprise," the Tottenham manager told a press conference.
"How can a game be scheduled after two days, immediately putting the players' careers at risk with injuries?
"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 and Chelsea, when I was at Chelsea, and I spoke the same way.
"The second day of recovery is the most dangerous day for a player to pick up an injury.
Source: PA
Source: PA