Yes, it sucks. I have it happen on all my teams, but as I dont have much luck in Cup it really only bothers me with League. I do have one set of matches 2 hr fifty three minutes apart. Not going to bother sending to Support, but if you really hate it you should let them know, enough complaints could change the system (eventually)

And SactoRepublic gets to play Pikachu and another Forumer on the same day. twice this season. It makes me think there's an evil elf in charge of scheduling!!