After Ivan made a wish into observing other people's personalities and lives, they went to Dimmsdale Elementary and met up with Chester asking him about his own point of view in life. As he explains, Ivan viewed his life as he talks inaudibly.
Chester along with Timmy, his fairies, A.J. and Tootie introduce Ivan to Mark Chang and later on helped defeat Princess Mandie and prevent her from destroying the Earth after Ivan was exposed while he was disguised as Mark.
Chester briefly appears during the a new and bad looking Dimmsdale after Timmy and Ivan wish themselves into the world of television, leaving Vicky into taking over the world leading to a bad future where Chester's future self alongside a future A.J., Timmy and Tootie travel to the past preventing all of this from happening.
Chester alongside Timmy and A.J. was brought along with Ivan after he became a musician thanks to Britney Btritney. Later on, the three were dumped by Ivan when he let fame and fortune was getting the best of him. When Ivan came to his senses, he apologizes to his friends and the four did a musical number at Mr. Bickles' class.
Chester along with the other Squirrely Scouts made a bet with the Cream Puffs into finding the rabid red-headed squirrel. Little did they know, it was Neptunia who was surrounded by her phobia of standing in the middle of the forest and turned rabid.
Chester and friends help Timmy into traveling to the 2nd Dimension where he meets his counterpart, where he and his friends are rebels against their Turbo Thunder. He and A.J. had a conversation with Veronica revealing that they knew of her secret crush on Timmy and promise to keep it a secret.
Chester introduce himself to Sally as she and Timmy switch schools for the day to see which is better. He along with the other kids at Dimmsdale Elementary congratulate her into exposing Mr. Crocker stealing the class movie and trying to frame her. This is Chester's first and only speaking role in the spin-off was well as his last appearance.