Here is the full list of all 15 You Have to Win the Game achievements. It takes around 2-3 hours to unlock all of the achievements on Windows.
Collected every money bag.
Traversed every room.
Acquired the Crimson Aura.
Acquired the Cerulean Aura.
Acquired the Springheel Boots.
Acquired the Spider Gloves.
Lost the game in any mode.
Won the game in any mode.
Won the game while wearing sunglasses.
Won the game as a cat.
Won the game in any mode with a 100% rating.
Won the game in any mode in under ten minutes.
Found Sammy and Lara a.k.a. Princess Boopypoo and the Countess von Flufflebutts a.k.a. I put my cats in a video game because I am five years old.