Doug gets a letter from his school and panics when he sees it's addressed to his parents. Since he's doing poorly in math, Doug immediately assumes that it's a failing notice! So he does everything to find out what the letter says and avoid his parents from seeing it. If that wasn't enough, Patti is trying to tell Doug something and get her message to him.

Chalky e Doug têm exatamente as mesmas respostas em uma prova de inglês e a suspeita do Sr. Bone e da Sra. Wingo é que Doug colou, pois Chalky é "perfeito". Doug começou a procurar Chalky e percebe que ele está o evitando. No final quem cola é Chalky, pois ele tem tantos cursos, prêmios e troféus que não teve tempo de estudar e faz uma prova extra. / Doug consegue o que sempre quis um convite de Patti, para o cinema. O resto da escola pensa que é namoro, os dois também. Mas o episódio termina eles quase se beijando e Patti vai para casa.

Doug is accused of cheating when he and Chalky score identical marks on a test. He is given one day to confess or he'll have to take a re-test. Doug knows he didn't cheat so he tries to talk about it with Chalky, but he keeps avoiding Doug.

Patti asks Doug to go with her to the movies, and now everyone at school is teasing them about dating. Even Doug wonders if it is really a date or not. In order to find out, Skeeter goes through dating scenarios from a book with Doug.

Doug's Bluff Scout Troop #617 has to raise money for new canoes, so they sell ""Bluff Scout Booster Bars"" door to door. But after being rejected by everyone, Roger offers a new way to sell the bars, which Doug doesn't agree with. Then when Doug sells a bar to Mr. Swirly, he realizes the problem of why the bars taste so horrible.

Doug se impressiona com os presentes que Beebe ganhou. Phil, o pai do garoto, sente-se pressionado em conseguir dinheiro para comprar um presente melhor para seu filho, e decide vender seu estúdio fotográfico. Inicialmente, Doug fica animado, mas quando percebe os efeitos em seu pai e na família, descobre que o dinheiro não compraria a felicidade. / ...

A/B) When a spooky new amusement ride, Blood Stone Manor, opens up at Funkytown on Halloween night, Skeeter wants to check it out instead of trick or treating. Doug reluctantly agrees to go, but when the park closes before their turn comes up, Roger convinces them to go on the ride anyway. Once on the ride, Roger scares Doug and Skeeter big time, so it's up to them to scare Roger back!

Doug é nomeado o novo tesoureiro da classe, mas ao encontrar Willy White, filho do prefeito de Bluffington, fazendo campanha, entra na disputa sabendo que praticamente não teria chance. Na eleição para a prefeitura, Tippy Dink vence o Sr. White.

Doug becomes the victim of a contest scam that promises to make him rich. But after trying so hard and paying a lot of money, Doug later realizes he may not be as close to winning as he thinks.

Episódio especial. Beebe acusa Costelinha, o cachorrinho de Doug, de atacá-la. Preocupado, o garoto faz de tudo para salvar a pele de seu companheiro. Ele e Judy compram um chapéu, mas o ex-prefeito White e Bill Bluff armam um plano para que Costelinha não incomodasse ninguém. Em julgamento, o cachorrinho é "condenado" a passar um período num canil. Abalado, Doug é impedido de visitar Costelinha, não se contém e começa a chorar. O garoto convence o tribunal a liberar Costelinha a voltar à cena do "crime" para mostrar o que havia acontecido de verdade. Beebe cai no gelo, e o cachorrinho resgata a garota, deixando Doug orgulhoso.

Doug acha na rua US$ 14,47 e pesquisa a dona dele até achar. / Judy arranja um novo namorado e ela pensa que a sua família é sem-graça. Theda vira uma palestrante, Phil, um pirata e Doug, um mordomo. Chateado, o garoto pula na lasanha e estraga tudo. Mas no final tudo se acerta.

Doug beats Patti in a bowling match, and Skeeter tells everyone about it. Doug gains popularity, but feels bad about beating Patti everytime they play a game. It seems Patti is having a losing streak and is upset about it.

Doug and Skeeter go digging for artifacts when they get assigned to research Bluffington's history. They soon get into trouble though, when they are caught digging on the Bluff estate even though they didn't know.

Skeeter gets a high score on an intelligent test making him a genius, and Doug is convinced Skeeter got the wrong test results. But soon Skeeter starts to spend less time with Doug and more time thinking about going to college, and Doug thinks he's lost his best friend.

All of Doug's friends have cool bikes, but Doug hates his--until he discovers that someone has stolen it. He thinks about who could have taken it, and wonders if one of his friends is a theif.

Doug and Judy get into a fight and blow their big chance to stay alone in the house while their parents are on vacation. Instead, they're cursed with the very, very strict baby-sitter, Mrs. Stintson.

A/B) Porkchop has been mistakenly accused of attacking Beebe and Doug has to try and clear his best non-human friend out. Unfortunately, former Mayor White, and Bill Bluff are determined to make sure that Porkchop never bothers anyone again. After a trial in court, Porkchop is sentenced to a dog pound for bad dogs. Then, Doug convinces the court to let Porkchop return to the scene of the crime to show them what really happened.

An envelope of money falls from a speeding car and Doug finds it with a huge fortune in it. Doug hands it in to the police and everyone makes fun of him for doing it. After no one claims the money, the police tell Doug he can keep the money. When Doug discovers who the real owner is, he must choose between what's legal and what he knows is right.

Theda invites Judy's new boyfriend over for dinner, but Judy is embarrassed by her boring family, especially Doug. So she decides to ""spruce"" things up around the house.

Doug is having his first house party, and he is very nervous about it--especially when he sees how his parents are planning for it. But when Roger suggests to play Truth or Dare, Doug hopes it makes his party better.

Skeeter exaggerates about how Doug can ride on a horse and Doug lets his friends believe the lie. But then Roger challenges Doug to show them, and Patti suggests they all go to a dude ranch to settle the argument. Since Doug can't ride a horse very well, he's nervous about going to the ranch.

Doug and his friends are getting ready for the end of sixth grade and are graduating from Bluffington School. Doug feels a bit sad about leaving so he tries to find Principal Buttsavitch to talk to him. But when he finds out that Roger is as reluctant to leave the school as he is, Doug convinces Roger (and himself) that the new school will be great.

As the summer begins, the Funnies plan to drive across the country to visit the Great Painted Gorge. Phil is committed to keeping to a schedule, but Doug and Judy convince him to stop at several tourist traps along the way. The family isn't having any fun on the trip, until they finally reach the stop that makes it all worthwhile.