Credit to: @FleurPotterWatson
She also has a fact book and it's amazing, you should read it!In the first book there were 7 challenges to get to the Philosopher's Stone. They all represent each book.
First, they see Fluffy. Fluffy's owner is Hagrid and it's the first time the Golden Trio met Hagrid. Also the story is based around Hagrid in the 1st book.
Then, the Devil's Snare. The Devil's Snare being a plant might represent Mandrakes, and Hermione is the only one that doesn't get trapped and helps Harry and Ron. In The Chamber Of Secrets (even though Hermione is trapped this time) Hermione helps Harry and Ron and without her help they wouldn't be able to find a way to stop the Basilisk.
The Flying Keys is the only room without any danger. It also happens that Prisoner of Azkaban is the only book where Voldemort doesn't try to kill Harry. And in this room The Golden Trio uses brooms to get the key, in Prisoner of Azkaban Quidditch games are more detailed.
The chess game represents a tournament, where you can die. Sounds familiar?
The stinky troll in the room probably represents Umbridge :p. In this one not much happens because Quirrel is possessed by Voldy. In the Order Of The Phoenix Harry is the one that is possessed by Voldy.
Snape's obstacle was the puzzle with potions, which might represent Slughorn, and the increase of detail in Potions.
And finally Dumbledore's obstacle, the mirror. In the Mirror of Erised Harry sees his parents which might represent Harry seeing his parents using the resurrection stone. And in this room it's the first time Harry fought Voldemort and in the Deathly Hallows it was his last time fighting him.

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Harry Potter Facts
AcakDo you think you know about the amazing magical world of Harry Potter? Well think again. Here is Harry Potter facts you might not know!