Win, Lose or Drew! (Japanese: ハルカ！ポケモンコンテスト初挑戦！！Haruka! The First Pokémon Contest Challenge!!) is the 35th episode of the Advanced Generation series, and the 309th episode of the Pokémon anime. It was first broadcast in Japan on July 24, 2003 and in the United States on May 29, 2004.
May enters Beautifly in the beauty contest, but Team Rocket is too late to enter their Dustox. At the competitions, the person in line right before May is none other than her rival Drew. Drew's Roselia gives an excellent performance, netting him an extremely high score. May is more determined than ever to beat Drew.
Meanwhile, Team Rocket is busy holding a "charity drive" scam for PokéBlocks. A little old man stops to talk to them about PokéBlocks. The contest is heating up with a Milotic stealing the show. May is up again in the contest and she and her Beautifly toss a disc back and forth, like they practiced before.
In the next round, she has to battle Drew who defeats her. He then looses to the contestant with the Milotic. May and Drew part on good terms and the scene ends with the old man still intently talking to a slumbering Team Rocket about PokéBlocks.
May runs towards the Contest Hall with Ash, Pikachu, Max, and Brock following her. May runs inside and is relieved to find out that she has just made the cutoff time to sign up. They then find out that they have three hours until the Slateport CityPokémon Contest starts and Brock asks what they should do. Ash says that they should eat because he is hungry after the run. After they leave Jessie and James walk in and perform their motto. The lady then informs them that they have just missed the sign up time, much to Jessie's disappointment. Jessie, James and Meowth walk outside and wonder what to do. As they are sitting there they see a male Trainer and his Poochyena training. The male Trainer then gives his Poochyena some Pokéblocks giving Team Rocket the idea to sell Pokéblocks. Meanwhile, the Slateport Contest is about to get underway as Vivian walks out onto stage. She presents the Slateport Ribbon and introduces the panel of judges, formed by the Chief of the Pokémon Activities Committee, Raoul Contesta; the President of the Pokémon Fan Club, Mr. Sukizo; and the operator of the Pokémon Center, Nurse Joy. Backstage, May is anxious and her nerves are beginning to get to her. Ash, Max, and Brock comfort her as Drew smiles from around the corner.
The Appeals Round begins and, one after another, Pokémon Coordinators take the stage to showcase their Pokémon in such a way that their appearances and skills are highlighted. Soon it is Drew's turn and he tells his Roselia to use Petal Dance and then Stun Spore as Vivian comments on how beautiful it is. Drew earns a 29.4. Outside Team Rocket is dressed up and ready to sell, but have no Pokéblocks. They are thinking about stealing some from the contestants, but change plans when an old man walks up and offers to teach them the secrets about Pokéblocks. They immediately agree, excited about learning secrets. Back at the arena, Drew walks over and begins to talk to May. They are interrupted by Robert as he and his Milotic begin to perform. Max comments that many say that Milotic is the most beautiful Pokémon and Brock agrees. Milotic uses Safeguard and glows a beautiful green. May is now next. She walks out onto the stage nervously. Vivian announces that this is her first Contest. May gets ready to send out Beautifly but falls. Vivian asks if she is alright and May replies yes, getting to her feet and releasing Beautifly. May throws the frisbee and Beautifly uses String Shot and hits it back. They go really well until the last one where May almost drops it after Beautifly uses Gust. May then tells Beautifly to spin and use Silver Wind creating a Silver Wind tornado. Drew is impressed and May earns a 24.9 much to her disappointment. May walks backstage and Drew hands her a rose, causing her to blush, until he explains that it is for Beautifly and not her, before saying that she still has a lot of training to do.
The old man is still talking to Team Rocket and all of them but James are asleep as he talks about spicy-flavored Pokéblocks. James is trying to take notes. May and Drew watch as the eight Coordinators moving on to the Contest Battles are revealed, including May, Drew and Robert. Brock worries that May has not had enough experience battling. May and Drew are facing each other as the second round match-ups begin. May sends out Beautifly and Drew sends out Roselia as the battle begins. Drew has Roselia use Magical Leaf and Beautifly counters with Gust. The attack hits Beautifly, injuring it. Roselia uses Stun Spore but it doesn't affect Beautifly. Beautifly sends out String Shot but it is reflected by Roselia's Magical Leaf. May orders Silver Wind but it is reflected by Petal Dance. Drew then orders Solar Beam and May desperately tries to reflect it with String Shot, but it hits Beautifly, severely injuring it. With only half the time up, the judges call the battle off. Drew is the winner and moves on to the next stage, much to the disappointment for May and her friends. May is backstage crying as Ash and friends try to comfort her.
Drew is battling Robert's Milotic but not having much luck. Milotic uses Iron Tail and Roselia sends out Magical Leaf, but Robert cuts through it with Twister. Robert is declared the winner and he goes on to win the whole Contest. May is cheering along with everyone else, having gotten over her sadness. As Drew is leaving, May runs out and tells him that she will win next time. Drew laughs and tells her that they will have to see about that. Back with Team Rocket, the man is still talking and now all are asleep. The old man is still chatting as the episode ends.
Roselia's performance was similar to Dawn's Ambipom's performance in Team Shocker!, where the Pokémon disappeared from sight during their flashy big finish. However, unlike Ambipom, who didn't pass to the next round because of that, Roselia did.
This episode was the first to air in Japan after the theatrical release of Jirach: Wish Maker.
Drew is missing his sleeves in a short scene right after losing to Robert.
The old man explains to Team Rocket that Spicy Pokéblock increases a Pokémon's Smartness. However, in the games, it actually increases Coolness.