Cruisin' for a Losin' (Japanese: ポケモンコンテスト！ルイボス大会！！ Pokémon Contest! Rubello Tournament!) is the 38th episode of Pokémon: Advanced Challenge.
May, confident in her Pokémon, enters the Contest with Drew and Savannah. While all three manage to pass the first round, May's Bulbasaur becomes nervous, which shakes May's victory. May tries to get Bulbasaur to battle, but this does not impress the judges.
Team Rocket is kicked out of the building where the Pokémon Contest is to be held. Jessie is angry, although James and Meowth point out it is a big fake ribbon. The announcer, Vivian, introduces the judges for the Contest. Meanwhile, May tells Savannah to relax, else the Pokémon will feel nervous if she does as well, since she knows this from experience. Team Rocket wanders off and Meowth plans on selling fake Poké Blocks. A woman wants Jessie's ribbon, thinking it would look pretty on her Azurill, to which Jessie is interested in. May sends Beautifly, who uses Morning Sun, followed with Silver Wind. Later on, May leaves the stage and bumps into Savannah. May is certain Savannah will do a good job, as she goes to the stage. There, her fans, even Pikachu, cheer her on, making her embarrassed a bit.
Savannah sends Flareon, who uses Fire Spin, then uses Tackle to go through the fire. Next, Flareon uses Swift, then Ember, which gives the starts a red glow. Sandra is glad, as she advised her mom that combination. At the waiting room, May is glad Savannah did good, though Savannah admits she didn't have much faith in herself. May states Savannah will do fine, as experience is what matters in the Contest, which got May two ribbons. Drew chuckles, so May asks him what is so funny. Drew, however, tells her to think on the future and to forget what she won recently, even if May does not know what that means. On the stage, Drew arrives, making his fans glad he is here. Drew sends Roselia, who covers the stage with petals, impressing the judges. Drew snaps his fingers, which stops Roselia from using the move. Meanwhile, James and Meowth are sewing large ribbons. However, Jessie looks at one and asks them to repeat all over, since she can't sell underquality products for a high price. Meowth, however, reminds her they have been doing this for a long time.
The announcer shows the contestants, who are Drew, Savannah, May and Sonny. May congratulates Savannah for passing into the next round. However, the next screen shows May has to battle Savannah, which leaves the two stunned. As Both Coordinators polish their Pokémon, Savannah is terrified she has to face May. May tells Savannah that she needs to give her best, no matter who she battles and anything less would be an insult to the opponent. Savannah sees the truth in that and decides to do so, while May goes to give her advice on battling. Max, Ash and Brock go to congratulate May. Max wonders if May should give battling advice to Savannah, but May points out she has some experience. Ash states if Savannah needs some advice, she can ask him. May is angry, claiming Contest Battles are more complicated than Gym matches. Sandra points out Savannah should just go battle like she always does. May confirms she will be using Bulbasaur in the next round. Ash goes to give advice to May, but she feels insulted and walks away, which upsets Bulbasaur. Brock looks at Drew, who shrugs about May's problem.
James and Meowth is sewing the ribbons, even if they think they made enough. Jessie denies, thinking these profits would make them rich. Vivian states, due to the Grand Festival rules, all trainers must use a different Pokémon than they did in the first round. Sonny and Drew begin the battle, as Sonny sends Girafarig and Drew his Masquerain. Girafarig uses Iron Tail, but misses and Masquerain uses Bubble. Next, Masquerain uses Ice Beam, freezing the bubbles, followed by Hidden Power. The spheres, created by Hidden Power, bounce off from the icy spheres and fall onto Girafarig, immediately defeating it. Next are May and Savannah. Savannah sends out Lairon and May her Bulbasaur. Unfortunately, Bulbasaur is overwhelmed by the audience and it becomes scared, then goes behind May. Brock admits he knew something like this was going to happen, for May's arguing with Ash made Bulbasaur nervous. Brock points out May did not see Bulbasaur got upset, while Max comments May only cares for her winning streak.
On the stage, May tells Bulbasaur to get going or they won't have a chance. Bulbasaur does so, while Savannah, remembering May's advice from earlier, orders to Lairon to attack with Take Down. Despite May's efforts, Bulbasaur is frozen in fear and ignores May's command. This causes Bulbasaur to get hit, causing May to lose some points. May has Bulbasaur use Vine Whip, which wraps Lairon with vines. However, Lairon fires Shock Wave, which, through the vines, electrocutes Bulbasaur, who barely stands up. Bulbasaur is paralyzed, though Max recalls Shock Wave does not paralyze an opponent. Brock and Sandra point out Bulbasaur used the vines to grapple Lairon and the direct contact made a much greater damage, a strategy Sandra thought of. Lairon attacks with Metal Claw, defeating Bulbasaur and knocking May out of the Contest. Despite the loss, May refuses to give up, insisting that she's not done fighting. The judges intervene, pointing out where is May's concern for her Pokémon and that caring for their Pokémon's health should be the first priority for any trainer before winning a Contest, leaving May shocked that she lost sight of Bulbasaur's well-being.
A while later, May is alone in the park outside the area and apologizes to Bulbasaur for pushing to hard. May admits that she let her desire to win a Ribbon get the better of her and lose sight of what was really important. Bulbasaur, not wanting May to feel bad easily forgives her. Ash and Pikachu arrive as well, pointing at the screen that it is the final round, with Drew's Masquerain battling Savannah's Lairon. May is not in the mood, so Ash sits down and tells every trainer can get overconfident and have accidents like these. Ash gives May some advice: regardless if it is a Contest or a Gym match, she needs to bond with her Pokémon to win. He states once they remember that advice, they are both united and their desire to win is even greater. Seeing Ash is right, May thanks him for the advice. Lairon attacks with Metal Claw, but is negated due to Masquerain's Hidden Power. Lairon attacks with Shock Wave, but time has run out, making Drew the winner. Savannah is shocked, but sees they at least tried and thanks Lairon for giving its best. Drew approaches Savannah and helps her stand up, thanking for such a good battle. Later on, Drew receives the ribbon, needing one more to be able to enter the Grand Festival.
Team Rocket advertises the ribbons they made, but nobody is buying. The woman that bought the ribbon returns for the money, showing Azurill's ribbon is too big for it. During the evening, Savannah is happy, seeing she had so much fun today. Savannah still has one ribbon, recalling her victory before with Flareon and Lairon. She thinks of that moment, which brings her happiness, regardless if she won or lost. May realizes that her ribbons are proof how well her Pokémon did in their Contests. May hopes to see Savannah again, to face each other in a Contest. Brock claims they have to give 100%, but Sandra doubts that, since her mother has to save some energy for housework. Savannah replies that's what daughters are for and everyone laughs.
- Featured Pokémon: Ludicolo, Camerupt, Duskull, Mightyena.
- In the beginning of the episode, a classic Pokémon identification can be seen. In this case, it is a Magikarp.
- The Pokémon Trainer's Choice states that Camerupt would be the best choice to battle Ludicolo. It would actually be the worst choice because Ludicolo's Water-type attacks would be 4× effective on Camerupt as it is a Fire/Ground-type. Ground-type attacks are not very effective against Ludicolo and Fire-type attacks are normally effective. Both Duskull and Mightyena would be normally effective on Ludicolo.
- As with the previous episode, Erica Schroeder is listed in addition to Bella Hudson in the additional cast credits.