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A story arc that lasted from the 10th to the 29th of September in 1990.

It starts off with Hobbes "helping" Calvin with his math homework. When Calvin's mom sees him reading comic books and Calvin claims that he's all done with his homework and that he's doing just fine in class, Calvin's mom leaves to go to a parent-teacher conference with Miss Wormwood, which of course freaks out Calvin and makes him nervous about what Miss Wormwood will tell his mom (and what his mom will tell his dad).

After Calvin's mom gets home from her meeting with Miss Wormwood, she admits to her husband that it didn't go so well and they talk about what Miss Wormwood had said, Calvin's parents talk to him and tell him what Miss Wormwood told them: Calvin's not doing so well and needs to start putting more effort and spending more time on his homework, particularly when it comes to math. Calvin's dad comes up to help Calvin with his homework, but Calvin's very resistant to it -- he claims that learning math is irrelevant and that he can get along just fine without it. But his dad points out that it's not irrelevant and that pretty much all jobs require some form of math -- to try and get Calvin more motivated, his dad uses pennies to teach him basic addition and subtraction, which seemed to make a little more sense to Calvin.

The next time that Calvin's in school, he's much more confident in his math skills now (probably too confident) -- when Miss Wormwood passes out sheets for a math quiz, Calvin makes a bet with Susie Derkins: whomever of the two of them gets a higher score has to give the other a quarter. At first, Calvin's confident that he'll do great on the quiz and win his bet with Susie, but he gets stuck on the first problem ("6+5=___") and then gets lost in a Spaceman Spiff-fantasy. By the time he finally answers the first question (which he gets wrong), time's already up for the quiz -- Calvin, now rushing to finish his quiz, guesses on the rest of the questions before finally handing it in to his teacher.

Susie gets a perfect score on her quiz while Calvin ultimately flunks his -- later on, while talking to Hobbes about what happened, Calvin tries justifying what happened by claiming that the only reason he flunked was because he ran out of time. Also, since Calvin lost his bet with Susie, he had to pay her 25¢ -- but Calvin then claims that he "cheated" Susie by "only" giving her three dimes (which is 30¢) instead. Hearing this, even Hobbes points out that Calvin needs to get more serious about improving his math skills.