It's supposed to be unwinnable if that's of any consolation at all x3 It masquerades as a minigame challenge, but it's physically impossible to succeed at it. It's kind of supposed to make you despair, haha.
You can technically beat Simon in a sense, just not at the actual game of Simon Says >.< And even if you do defeat him, the story continues the same way regardless.
The different outcomes & cumulative effects of choices made throughout only become apparent right at the end of this one.
Sorry if the Simon Says stuff was jarring >.< The whole game is meant to be a bit mad. Thank you for checking this one out though :3