On the eve of the new millennium, everyone — except Dilbert — is making New Year's plans. While assuring everyone that the company is prepared for Y2K, Dilbert discovers that the computer mainframe's main processor isn't Y2K-compatible and all the company's systems will crash if it isn't fixed. Dilbert is rewarded for discovering this by being assigned to fix it, and he discovers that the system's original programmer was Wally. But have years of drudgework dulled his brain too much to be able to tackle this crucial task?

Dilbert thinks there are too many time-wasting holidays; Dogbert concurrently convinces Congress to abandon all holidays in favor of a National Dogbert Day.

Dilbert loses "the knack" for technology when he gets management DNA from accidentally drinking from the Boss's cup. His resulting mis-steps send the world back to the Dark Ages.

The pre-production—non-lab-tested—Gruntmaster 6000 is scheduled to be tested by a Texan family.

Dilbert is fired from his job when he is suspected of being a spy for a rival company (which was a rumor cooked up by Dogbert's online newsletter) and gets hired at a company that actually treats their workers like people.

The annual company picnic comes around and so does the softball game between Marketing and Engineering. This episode is based on Romeo and Juliet.

Dilbert is forced to be a charity coordinator for the "Associated Way" charity drive.

Dilbert and his co-workers find an empty cubicle and start dumping their obsolete computer equipment into it. To keep the marketing department from claiming the cubicle, they hack into the human resources database and create a profile for a fake engineer named Todd. The plan backfires when Todd is named project leader and develops a messianic reputation.

Dogbert becomes rich and famous by writing a best-selling book about an imaginary disease, 'Chronic Cubicle Syndrome', and Dilbert finds himself saddled with the job of devising a cure.

Dilbert's home is chosen as the location for an off-site meeting when a dendrophile sues his company because of their deforestation policies.

Dilbert tries to end world hunger by creating a new, safe, artificial food, but it tastes so bad that even people dying of starvation refuse to eat it – until his mother gets involved.

The Gruntmaster 6000 prototype is put to the test by an evil masked test engineer named Bob Bastard.

When Dilbert wakes up after another night of having the egg dream, he discovers he isn't the only one to have had the dream. His fellow employees tell him about The Chicken Man, a guy who turned into a chicken after he was put in charge of a product that he was unable to name. Dilbert soon finds himself in the same situation.

Dilbert, Alice, Wally, Dogbert, and the Pointy-Haired Boss take a business trip to Elbonia. Alice and Dilbert attempt to free the Elbonian people (Alice adopts an Elbonian baby while Dilbert introduces the workers to human rights) while Wally becomes a prophet.

Dilbert is unwillingly promoted to management and given an assistant, sparking a showdown with the other engineers.

After a heated debate, Dilbert and the building's security guard trade jobs to see who can do the other's job better. Dilbert quickly finds himself in over his head when he discovers an illegal casino being run underneath the building.

Dilbert's attempts to design a Furby-style children's toy go horribly awry when the toys gain sentience and mutate into hideous but benevolent creatures that want independence.

Dilbert and Alice must work together to stop a rival team led by the legendary "Lena" from stealing their ideas and presenting them to the Boss as her own.