In the series' first Christmas episode, "A Very Special Family Guy Freakin' Christmas", Stewie is told he will be playing the role of Jesus in the town's Christmas pageant. He becomes paranoid after being told that Santa is watching him. After speaking with a mall Santa, Stewie agrees to be good so that he can receive plutonium for Christmas, even playing the role of Jesus in the pageant.
In "Road to the North Pole", Stewie plans to kill Santa after being ignored by a mall Santa. After seeing that Santa is in a bad condition, he and Brian decide to deliver his presents themselves. Stewie also sings in the songs of this special, "All I Really Want For Christmas This Year" and "Christmastime Is Killing Us!".
In "Jesus, Mary and Joseph!", Stewie plays baby Jesus, in the parody of The Nativity Scene.
In "Christmas Guy", Stewie's Christmas wish was for Brian to come back to life. He was able to find his past self, ending up in his time, where he was able to access time travel once again and save Brian's life.
In "The 2000-Year-Old Virgin", Stewie had a minor role at the end of the episode. Rupert gave him a Joni Mitchell CD for Christmas, disappointing him because Stewie had observed Rupert buying a heart-shaped necklace and wrapping that up as a present for someone, leading him to wonder, if he got a CD, then whom was the necklace for, and it is revealed to be for Mayor Adam West.
In "How the Griffin Stole Christmas", Stewie discovers that Brian has been crashing office Christmas parties for free alcohol and is about to attend one. When attending a party, he tries to impress a girl, but it fails. Stewie arrives to survey how Brian is failing at his malingering, but decides to stay at seeing the free food. During Christmas parties they attend at the printer company Printex, Stewie makes a stir that pleases the employees and the employer who gives him a job. Later on, Stewie discovers that his riot has gotten a woman fired when he checked to see if her Internet is slow. Stewie soon realizes that working in an office is not all great, so he decides to spread some holiday cheer by giving out some $11,000.00 checks to the other employees before resigning from the office.
In "Don't Be a Dickens At Christmas", Peter was shown a future, where Lois remarried someone else. Stewie was shown as a young adult, who didn't go to college and became really fat. He said that he browns four boxes of Jimmy Dean Pure Pork Sausage for his breakfast.
- "A Very Special Family Guy Freakin' Christmas"
- "Road to the North Pole"
- "Jesus, Mary and Joseph!"
- "Christmas Guy"
- "The 2000-Year-Old Virgin"
- "How the Griffin Stole Christmas"
- "Don't Be a Dickens At Christmas"