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Conflicts in episodes
In his debut episode "Band Geeks," Squidward receives a call from Squlliam over the phone who is bragging about his rich and successful life. He then says that he is going to be performing at the Bubble Bowl, knowing Squidward isn't. However, Squidward lies saying he will perform there and goes through three days trying to get everyone else to perform right. Squilliam is seen again near the end of the episode where he is eager to see Squidward fail. Squidward trying to lie his way out again by saying his band "died" but they soon appear. However, Squlliam fainted in shock after hearing Squidward's band perform greatly and Squidward jumps up in excitement finally earning a win over his rival.
In "Squilliam Returns," Squilliam appears at the Krusty Krab where he once again runs into his rival. Squilliam once again brags to Squidward on his success and asks what Squidward has done since high school. Squidward says he works in a restaurant but Squilliam quickly knows that Squidward works as a cashier and laughs at him. Squidward lies once again saying he owns a five star restaurant which shocks Squilliam for a second. Squilliam then agrees to eat at the five star restaurant and treats all of his fans much to Squidward's horror. Squidward then desperately tries to get the restaurant together but it is thanks to SpongeBob who helps out. Squilliam is impressed by Squidward's profession but more so by SpongeBob and asks for his name. However, SpongeBob starts to freak out and the five star restaurant is soon wrecked and Squidward finally reveals himself as a cashier. Squilliam then says he is also a cashier but lies about it to get at Squidward then leaves. This is Squilliam's first shown victory over Squidward.
In "House Fancy," Squidward is at home watching his favorite show House Fancy. However, he soon receives a call from Squilliam who is actually on the show with Nicholas Whithers. A jealous Squidward is forced to watch as his rival is being praised over his nice house and just as Whithers was going to say that Squilliam had the fanciest house, Squidward calls over the phone saying his house is more fancier than Squilliams. Whithers then decides to check Squidward's house for himself and Squidward goes to great lengths to get his house into shape. Squidward's house was destroyed but, surprisingly, Whithers adores the house. Nicholas Whithers then crowns Squidward as House Fancy Prince much to Squilliam's displeasure. Squilliam then falls onto the ground and cries earning another win for Squidward.
In "Keep Bikini Bottom Beautiful," Squidward was forced to do community service for "littering". Squilliam then finds Squidward and jokes on him saying he is doing community service. Squilliam then shows Squidward his giant statue for cleaning up Bikini Bottom which upsets Squidward. Squilliam finally receives his first ticket after his statue was destroyed pleasing Squidward. However, Squidward ended up with a ticket which actually results this feud in tie.
Squidward and Squilliam don't show much interaction with one another in "Professor Squidward." However, Squidward, upset that Squilliam gets to teach his own class, impersonates Squilliam so that he can teach the class. Unfortunately for him, Squidward gets arrested for "impersonating a genius" and Squilliam can be seen smiling. This is considered a win for Squilliam.
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- Out of all of the times that Squidward won or lost to Squilliam, SpongeBob was greatly responsible for it.