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.
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, landing on the stage with a graceful curtsy. Roselia follows up with a twirling Stun Spore and Magical Leaf combination. For its grand finale, Roselia disappears into a blizzard of petals before slicing them with a Magical Leaf attack for a dazzling display. As Vivian comments on how beautiful it is, Drew earns the highest score yet, with a 29.4. Drew walks backstage 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, causing it to radiate with a green glow. Ash rushes out to check his Pokédex on Milotic, and Max adds that it is considered the most beautiful Pokémon. Milotic fans out its tail to show off its magnificent scales to the roaring crowd. The last entrant, May is now up. 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 a frisbee and Beautifly uses String Shot to whip it back. May orders Beautifly to use Gust to send the frisbee back, though May almost fails to catch it. May then tells Beautifly use Silver Wind while spinning, which creates a Silver Wind tornado effect. May ends her performance with a bow and Beautifly landing on her head. Drew is mildly 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. Outside Team Rocket are 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 approaches and offers to teach them the secrets about Pokéblocks. They immediately agree, excited about learning the secrets. The old man's lecture causes James to fall asleep as he tries to take down notes.
May and Drew watch as the eight Coordinators moving on to the Contest Battles are revealed, including themselves 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 calls out Roselia as the battle begins. Drew has Roselia use Magical Leaf and Beautifly counters with a Gust. The manoeuvre works momentarily, but the Magical leaf still injures Beautifly, costing May some of her valuable points. Drew informs May that Magical Leaf is a move that always hits. Roselia follows up with Stun Spore, but it doesn't affect Beautifly. Beautifly sends out String Shot, though it is shredded by Roselia's Magical Leaf, causing May to lose more points. May orders a Silver Wind, but it is countered by Petal Dance. Beautifly manages to fly up to avoid the petals as Drew then orders Solar Beam. May has Beautifly use String Shot, but Roselia has fully charged its attack and scores a direct hit on its opponent. Beautifly looks worse for wear as it drops to the battlefield in exhaustion. 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. The boys find May backstage as she struggles to control her tears. They try to comfort her, admitting that it is tough losing.
May's focus turns to the television screen as Drew takes on Robert's Milotic in the next round. Vivian reveals that Roselia has already taken some hits, and Robert appears to have the upper hand. Milotic lashes its opponent with an Iron Tail. 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 leaves the Contest Hall, 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 continues to tell them all about Pokéblocks till nightfall, unaware that his students are fast asleep.
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.