The main kid group (except Carolina) and Martha are walking along the sidewalk, and T.D. is reading a sports magazine. Then, they decide to race to the Lorraine house (with Martha as the referee, since she runs faster than the kids) and the winner gets a glass of milk.
T.D. wins, and annoys his friends by bragging about it. In Helen's room, she shows her friends her (and her dogs') trophies, which saddens Milo, since he's never won a sport before. His friends point out that he's younger than them, but then Martha reveals that T.D. still won many things when he was seven. Helen then points out that Danny has never won a contest, only for him to enter and reveal that he's just won a bowling league.
Later, Helen and Martha pass the Lee house, and they hear Milo shouting, "Whoa!". They go to his backyard to find him playing with clubs. He explains that he's practicing because he wants to win a gold medal as an Olympic club swinger, but Helen points out that his book says that club-swinging hasn't been in the Olympics since 1932. She asks if he could try a normal sport, but Milo reveals that he has and disliked them all. Helen suggests he create his own, so he agrees.
He invites his friends over to test their stamina by seeing who can crabwalk to the park, and the prize is a homemade trophy. However, Alice wins instead, so the next day, he invites his friends over for a corn-shucking contest. Truman wins, so Milo comes up with a new contest: make three laps around the yard, while tossing a ball between their hands and balancing a book on their heads. Dropping one of the objects doesn't disqualify a player, but it does require them to stop and pick it up.
Now, Milo admits that he's been enjoying inventing the sports, but he doesn't know what else to come up with. T.D. suggests something like a triathlon, so Milo comes up with a "five-athlon". The five steps are filling ten, water balloons with squirt bottles, throwing them all at a monkey poster, running ten times around the yard while doing the chicken dance, frog-hopping around the tree three times, and crossing a balance beam.
They do it, and he finally wins. Later, T.D. submits the "five-athlon" into his sport magazine.
This episode provides examples of
- Accessory-Wearing Cartoon Animal: The monkey on the poster wears a bowtie.
- Ahem: T.D. clears his throat to try to get Martha to go along with his lie that he never won anything at age seven.
- Alliterative Title: T.D.'s magazine is called Sporty Sport.
- And Your Reward Is Edible: Discussed by Danny, who says that he won a pizza for bowling.
- Athletically Challenged:
- Milo is established to have never won a sport in his life.
- Danny wins his first sport (bowling) in this episode despite being a full-grown man in his thirties or forties.
- Buffy Speak: Milo's version of a triathlon with two extra parts is "five-athlon" ("quintathlon" would be more linguistically consistent).
- Compliment Backfire: T.D. says that he couldn't have won the race if only his friends weren't less swift than him, which offends them.
- Continuity Nod:
- Two of the trophies Helen won are from when Martha won Best Talking Dog in a "phony contest" (in "Best in Show") and when Skits won a flying objects contest (in "Martha and Skits").
- Milo mentions that he has a lot of stamina from carrying a heavy backpack around his old neighbourhood. This was first revealed in "Camp Truman".
- Department Of Redudnancy Department: T.D.'s magazine is titled Sporty Sport.
- Does Not Like Spam: Discussed when Danny reveals that he won a bowling league and got pizza as a prize, only for Milo to run away in anger since that leaves him the only person he knows of to have never won anything. Seeing as Danny didn't hear the conversation, he has no clue what angered Milo, so he says, "Milo doesn't like pizza?".
- Innocently Insensitive:
- Truman accidentally makes Milo even sadder when he expresses happiness about having won a bowling match.
- Danny accidentally angers Milo by revealing that he's won a bowling match, because Helen had just reassured him by saying that Danny had never won anything.
- The Pratfall:
- Milo falls on his behind while playing with the clubs.
- Alice falls on her behind twice at the beginning of Milo's third contest.
- Running Gag: Martha keeps wanting to make dog scratching into a contest.
- Slapstick: T.D. keeps tripping on things when he tries to walk along reading.
- Sore Loser:
- Downplayed when Milo is disappointed at having never won a sport in his life.
- Inverted when Milo's friends lose at the games he invents and become Sore Winners due to wanting Milo to win. They even apologise for winning.
- Speak in Unison: Milo's human friends chant his name in unison when he finally wins.
