October is the tenth month of 2019. It began with Chris butting heads with Ben Saint as he took issue with Ben's use of his characters. Eventually, however, the two's animosity plateaued and Chris would resume his regular actions. At the same time, however, Jacob Sockness would again return to try and influence Chris.
- 1 October - Barb turns 78.
- 3 October - Displeased by how Ben Saint depicted Night Star in his webcomic, Chris releases his own amended version and demands $300 from him for "using our name and individuals for the greedy gains accrued".
- 6 October - In preparation for BABSCon, Chris enlists Aly Hirschberg's help to request £5,000 from his TRUE and LOYAL fanbase.
- 10 October - A ween makes a video. egging chris house
- 12 October - My Little Pony: Friendship is Magic airs its final episode. Meanwhile, Chris berates his financial supporters on Twitter, justifying that his trading cards are an adequate alternative to the comic he is paid to create.
- 15 October - While responding to Ben Saint, Chris indicates his support for 2020 United States presidential candidate Andrew Yang. This support is later retracted in favour of Lisa Simpson.
- 16 October - Sockness regains Chris's favour, returns to his post as his exchequer and declares that he will try again to visit him about Halloween. This does not come to pass.
- 19 October - Barb experiences high blood pressure and has Chris take her to the ER; Chris reports that doctors don't find an issue and chalks it up to stress and magical energy from the Merge.
- 20 October - In a YouTube comment on Part 24 of Chris-Chan: A Comprehensive History, Chris revises his past, claiming he had known all along that Alec Benson Leary was a troll.
- 26 October - The newest Chandler kitten, Baby, is mentioned by Chris in passing to be ailing from a "nasal problem" while he live-streams himself playing his own card game.
- 31 October - Halloween.
- Joey Vance visit