Simon, Theodore and Dave dry to prevent Alvin from going to the karate championship as they fear he might get hurt. Alvin and Theodore believe that Simon is dave's favorite so they try to prove that they can beat Simon at anything
After Simon fails a test , he decides to go on strike and that includes moving into a tree but the chipmunks and chippettes try to convince him to come back. Alvin fears that once Dave has read his report card , he won't get his new video game so he tries everything to make sure that Dave doesn't receive his report card.
Miss Croner leaves Theodore in charge of looking after her cats while she's gone out of town but he can't let his brothers or Dave find out / the chipettes think that the chipmunks are all addicted to one item they each like but they disagree so they do a test to see who can go the longest without touching their favorite items.
The chipmunks and chippetes think that alvin spoils shows but Alvin disagrees so they all bet that Alvin can't stop talking for 24 hours but he proves them wrong / Theodore wins a goldfish at a fair and loves it so much but Alvin and Simon thinks that he might be dead so go out to replace him.
Miss smiths pairs everyone in the class up to look after their own robot baby in order to experience a parents life but Alvin and Brittany struggle with the task. The coach decides to enroll Alvin , Simon and Theodore into a ballet class as their team can't beat Derek's team.
Theodore shows Alvin what life without Simon would be like but Alvin finds it quite boring. Theodore is winning the contest of the cutest chipmunks but Alvin tries everything he can think of to make sure he gets declared as the cutest chipmunk.
Theodore creates a handmade vest for Dave, but Dave's too embarrassed to wear it/ Theodore finds a winning lottery ticket and all his friends and family members try to influence what he spends the money on.
Someone has been painting all of the walls and it is up to the chipmunks and chippettes to find out who it is / Theodore finds a lucky clover and explains that lucky things happen to him when he's holding the lucky clover, everyone believes it except Alvin but afterwards he wants it.
When the chipmunks get tired of Dave always telling them what to do , they decide to build a tree house in the backyard and live in it, when Simons experiment goes wrong, Alvin and Simon are magnetized to each other and struggle to cope with each other but they can't let anyone find out especially dave.
When Alvin, Simon and Theodore get stuck with miss Miller as a babysitter, they decide to get someone new but all of their choices aren't at all like they hoped they would be. When Alvin and miss smith get paired up they struggle to work together but in the end they found out that they're better working as a team.