October is the tenth month of 2019. It began with Chris butting heads with Ben Saint as he and the Watchmen took issue with Ben's use of his character. 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. She and Chris have lunch at the Wood Grill Buffet.
- 3 October
- Chris is displeased by how Ben Saint is depicting Night Star in his webcomic and releases his own amended version.
- The Watchmen continue to egg on Chris to confront Ben, particularly to ask Ben for money. Chris sends a DM to him demanding $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 fans.
- 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 favor, 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 Twilight Sparkle's Secret Shipfic Folder.
- 31 October - Halloween.
- Joey Vance visit
- Ben Saint DMs
- Children of Kefentse
- Geno Samuel DMs
- Midnight's Nightlings and Starettes
- The Place chats (October 2019)
- The Place chats (October 2019)#Birthdays
- October 2019 social media posts#Chris begins to rewrite Ben Saint's canon
- The Place chats - Ben Saint#3 October 2019
- Ben Saint DMs#DM'ing Ben Saint to demand $300
- October 2019 social media posts#Fundraiser for BABSCon
- October 2019 social media posts#Chris orders the Shipfic cards, snaps at customers wanting books
- Midnight's Nightlings and Starettes#Barbara's Trip to the ER
- Chris Chan Sonichu plays Twilight Sparkle’s Secret Shipfic Folder, Solitaire