The Football League has decided that Tottenham will play Aston Villa in the third round of the Capital One Cup on Tuesday, just two days after the north London club face Cardiff in the Barclays Premier League.
Given that Spurs play Tromso in the Europa League this 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.
Although he has a big squad at his disposal, Villas-Boas fears some of his players could suffer serious injury because of the close proximity between the Cardiff and Villa games.
"After this game we have not only the Sunday game but the Tuesday game, which I found as an incredible surprise," Villas-Boas told a press conference.
"How can a game be scheduled immediately after two days? It's putting the players' careers at risk.
"I find it absolutely incredible that we have to risk injuries to our players in a game that they play on that Tuesday.
"The second day of recovery is the most dangerous day for a player to pick up an injury.
"If this is not taken into account I think it's bad. Obviously other things have to be respected and 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."
Villas-Boas vented his anger at the Premier League two years ago when his Chelsea side had to play Wolves two days after they lost against Bayer Leverkusen in the Champions League.
This time it is the Football League that is in his sights as it is the organisation that organises the Capital One Cup.
The Football League defended the scheduling, pointing out that it would be unsafe to move Spurs' game to Wednesday, when West Brom and Birmingham are also playing in the Capital One Cup.
Both of those clubs are also playing teams (Arsenal and Swansea) that are in action on Sunday as well.
"There is a fixture congestion issue caused by three Midlands clubs being at home to sides playing on Sunday in the Premier League," a Football League spokesman said.
"In an ideal world all three games would be played on the Wednesday night, but for crowd safety reasons it is not possible.
"The only option that enables just one of the games to be moved rather than two is for the Aston Villa v Tottenham Hotspur match to be played on the Tuesday.
"It isn't anyone's preferred scenario but it is definitely the least worst option."
It is also standard practice to avoid Spurs and Arsenal having away games on the same day for fear of trouble en route to their respective matches.
Villas-Boas can take comfort from the fact he will be able to rest a number of players for the visit of Group K outsiders Tromso.
The Norwegian side only made it through to the group stages of the competition because the team they lost to in the play-off stages - Besiktas - were disqualified for match fixing.
Villas-Boas will be without Aaron Lennon because he is still struggling while Romanian defender Vlad Chiriches is, remarkably, still to receive a work permit even though his transfer from Steaua Bucharest was completed three weeks ago.
"We are waiting for the post to arrive for the player to be registered," Villas-Boas said.
"As awkward as that may look and sound, that is the reality.
"The player is frustrated with the situation but we can't do anything about it."