And the fall-out could get even worse, as the Premier League will turn down any request from Chelsea to wear the winners' badge if they become Club World champions.
Di Matteo, whose team face Liverpool today, said: "We are very happy to go to Japan. We've tried to postpone the Sunderland game to give us the best chance, but, obviously, the Premier League didn't agree to it as usual.
"So that's certainly going to put the strain on the players because we are going to have to travel after the Sunderland game and arrive basically three days before our first game in Japan.
"You would think the Premier League would have every interest in making sure they give you the best chance to be successful in Japan, which would reflect very, very well on English football and the Premier League. I'm very surprised about it.
"I can't get my head around it. The fixture list is very full, but where there's a will, there's a way.
"You see all the other federations trying to help their teams to do well in Europe and around the world. We've talked about this last season as well. This is one of the biggest trophies in international club football, if not the biggest.
"Travelling to Japan with nine hours time difference and arriving three days before, you want to do everything in your power to be ready for those games.
"We wanted to go a few days earlier, so the players have enough time to adjust to the new time zone.
"The team we play first in the semi-final will have already been in Japan at least a week.
"There have been ongoing discussions with the Premier League about it, but now we've heard there will be no postponement of the game. It's a big risk in terms of health and injury for the players.
"Maybe in England the tournament is not regarded as so big, but you speak to the South Americans, the Asians and everybody else that's involved - it's a massive, massive competition.
"The Club World Cup is as big as the Champions League for me, absolutely. It's massive. Winning that trophy would mean the world and we desperately want to bring it to Stamford Bridge."