The thing about My Senpai Is Annoying is that it’s a good series, but it rarely advances the plot. There’s been a total of 138 chapters and the romance between the two main characters has barely progressed. So, we’ll probably just get the one season.
That being said, I’m real excited for the anime because Doga Kobo will be animating, and I love their work. They do a tremendous job of animating cute stuff.