An underrated part of the Pokemon anime that few people talk about anymore is Pokemon Contests. During the Advanced Generation and Diamond & Pearl seasons, Contests were the vehicles for newer protagonists May and Dawn to shine, and were given equal narrative importance to Ash Ketchum’s routine League progression.
Fans talk a lot about Ash’s best battles, and rightfully so. But May and Dawn had some excellent battles that deserve more attention, even if they operate under a different set of rules. These battles listed here were the best that the Contest format had to offer, and proved that the anime could shine just as bright without Ash hogging the spotlight.
10 May vs. Zoey - Wallace Cup
This wasn’t even the main battle of its episode, but it was a perfect way to set up May as an incredibly tough final opponent for Dawn. Beating Dawn’s main rival under the bright lights of the Wallace Cup proved that May’s prowess was no joke.
Zoey’s Glameow had a nice few tricks in its bag, but May’s Beautifly had just the right counters for it. For every time Glameow showed out, Beautifly showed out harder. As hard as Zoey tried, May’s experience just won out in the end. As an undercard to the episode’s climactic battle, it did its job beautifully, both in a narrative and visual sense.
9 Dawn vs. Ursula - Daybreak Contest
Ursula was a different kind of coordinator, both in terms of personality and strategy. Her feisty attitude bled into her Contest battling style, hampering her opponents in unique ways. That brutal strategy was shown to full effect against Dawn at a Contest in Daybreak Town.
Prior to their faceoff, Ursula overheard her rival’s childhood story revolving around a nickname, “Diamond Dandruff” or Dee Dee. She replicated it in their battle, using her Plusle’s and Minun’s Electric-type attacks to get Dawn’s and her Pokemon’s hair all spiked up. Despite reliving the embarrassment of that memory, Dawn straightened up, ruined her Mamoswine’s and Cyndaquil’s Encores by having them attack each other, and perfected their physics-defying Flame-Ice combo, emphatically winning her the Contest.
8 May vs. Harley - Purika Contest
This rival of May’s had no issues with playing dirty, and he would do so for the pettiest of reasons. Prior to his debut Contest at Izabe Island, after learning that May didn’t know what a Cacturne was nor love the cookies he baked, he went full-Michael Jordan and took it personally.
He pulled no punches, from giving May bad advice for her upcoming battles to just straight up telling her he didn’t like her. Then, the pièce de résistance: playing a recording of Max telling one of May’s embarrassing childhood stories during their battle. While the shenanigans were good for a few points, May got serious and had her Bulbasaur knock out his Cacturne, winning the Contest.
7 May vs. Jessie - Mulberry Contest
This battle had no business being this good. While Jessie of Team Rocket, then going as “Jessebella,” wasn’t considered as serious a coordinator in the Advanced Generation seasons, she outdid herself at the Mulberry City Contest. She was an unexpected obstacle for May, who needed to win just one more ribbon to enter the Kanto Grand Festival. It didn’t help that Jessie borrowed Harley’s Pokemon to keep her on her toes.
It came down to the wire, needing overtime to settle. Even though May eventually won, this was the perfect way to set up Jessie’s improvement as a coordinator later down the line, when she actually started to win Contests in Sinnoh.
6 Zoey vs. Nando - Sinnoh Grand Festival
There were some very interesting matchups in the Sinnoh Grand Festival, and while Dawn’s battle against Jessie was pretty one-sided, Zoey and Nando’s was incredibly fun to watch. Even though Zoey managed to win this one, Nando was no slouch.
Each battler displayed their unique styles and great one-upmanship, using the other’s moves to their advantage. Even as a competitor, Dawn couldn’t help but be wowed by the performances both coordinators were putting out. While the main coordinator of the series wasn’t part of this battle, this semifinal match set the bar for the eventual final between Dawn and Zoey quite high.
5 Dawn vs. Lila - Celestic Contest
Even after breaking her slump for good at the Wallace Cup, Dawn’s journey ahead was far from smooth. One contest, in particular, had some extra weight to it, with Dawn having to compete against Lila, the Coordinator-turned-Stylist that broke her mother’s winning streak.
The pressure didn’t really get to Dawn, though. Even as Lila proved she knew her stuff, Dawn stuck to her guns and managed to make it a match. Tons of props go to Dawn’s Ambipom for fighting through both sleep and infatuation to win the battle for Dawn. If nothing else, this Contest proved that Dawn had the chops to match and even surpass her mother one day.
4 Ash vs. May - Terracotta Contest
It was only right that the Advanced Generation seasons of the anime ended with its two main protagonists battling each other. It might have been an unofficial contest with no real stakes, but it was a great way to show how far Ash and May have grown, and how much they learned from each other.
It was just as fitting that they fought with their Hoenn starters. Sceptile and the newly-evolved Blaziken put on a show at that Terracotta contest, showcasing the two Trainers’ differing battle styles. Despite the type discrepancy, the battle ended in a tie, showcasing them as effective equals while also demonstrating Ash’s skill as a battler.
3 Zoey vs. Dawn - Sinnoh Grand Festival
The Sinnoh Grand Festival final was an absolute spectacle. Even though Dawn lost to Zoey, who was probably still the better coordinator at that point, there was absolutely no shame in how she went out.
She fell behind in points early, but the way she fought back showed a lot of growth; a younger Dawn would’ve given up halfway through that bout. This was an excellent culmination of Dawn’s arc throughout her time as a main character, proving that she had a bright future ahead of her. The battle just so happened to be beautiful to the eyes too, with Zoey’s Gallade and Glameow and Dawn’s Piplup and Togekiss pulling all the stops.
2 Dawn vs. May, Wallace Cup
Not only was this a marquee matchup — it’s literally the two main coordinators battling in the Wallace Cup finals — it was also a huge benchmark in Dawn’s journey.
Part of the reason why May’s reappearance in Sinnoh was such a great plot device was that it provided Dawn with a figure to look up to. Seeing a coordinator as good as May going through similar struggles to hers inspired Dawn to try and break her slump. She did that in a stunning fashion by beating the Princess of Hoenn, in a very close fight too. This battle was also the series’ closest allegory to passing a torch, boldly giving the victory to the newer coordinator that the older one paved the way for.
1 May vs. Drew, Kanto Grand Festival
While the Hoenn Grand Festival was underwhelming, the Kanto Grand Festival made up for it, particularly with how it showed the dynamic between May and Drew. Drew was getting more and more insecure about May potentially being better than him, and his suspicions proved right as May beat him in an intense, wire-to-wire battle.
To May, this was a lot like Ash’s victory against Gary. Drew was one of May’s best rivals, partly because he was seemingly better than her at every step. To see May take the win this time, in the way she did, was the apex of her character arc. It’s too bad she got wiped out by Solidad in the very same episode.
NEXT: Pokemon: Every Different Design Of Ash Ketchum’s Hats, Ranked
