Like the others that replied, I am on windows and this is a new save, and sleeping does not trigger the event. I replayed it a couple of times, and it looks like doing the Holloween event before getting 20+ agility causes the problem. If I had to guess, since the Holloween event sends you to the mansion early, it's setting a flag that is conflicting with the progression after Speedy.
I found the bug! Your comments were a huge help. It turned out that playing the Halloween event before reaching 20 Agility triggered a switch that skipped several events, including the one that unlocks the next mini-game. Thanks to everyone who reported this issue; I’ll be updating the game shortly to fix it :)