Here is the full list of all 15 You Have to Win the Game achievements. It takes around 5-6 hours to unlock all of the achievements on Windows.
Lost the game in any mode.
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.
Acquired the Spider Gloves.
Acquired the Springheel Boots.
Acquired the Cerulean Aura.
Acquired the Crimson Aura.
Died once.
Collected every money bag.
Traversed every room.
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.