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.
Won the game in any mode with a 100% rating.
Collected every money bag.
Won the game in any mode.
Traversed every room.
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 Crimson Aura.
Acquired the Cerulean Aura.
Died once.
Won the game while wearing sunglasses.
Won the game as a cat.
Won the game in any mode in under ten minutes.