The Pokemon animated series is rife with heart-racing battles and eye-welling moments, and traditionally, the League battles get more traction than any others. For example, Paul versus Ash from the Sinnoh League Victor series remains one of the most memorable Pokemon battles of all time. However, contest battles have a different appeal altogether.
In the games, the contests are technical and have nearly nothing in common with the contests in the anime. The contest rounds and battles in the anime hinge on many things: the beauty of the performance, the technical execution, and how "in sync" the coordinator is with their Pokemon. In some ways, contest battling can be so much more difficult than traditional battling. The best displays of this style of performance battling are listed below.
10 Ash Vs. Kyle - The Sinnoh Wallace Cup
Although Ash is known for his League battles and more of a combat-oriented thought process, Ash's performance at the Wallace Cup on the banks of Lake Valor was one of the most impressive of the series and of the tournament.
His only issue was that he used Buizel throughout both stages (appeal and battle) and hence lost to Kyle, but not before Ash gave it his all. With his signature effort and boundless positive thinking, Ash was able to put up a heck of a fight against the more experienced coordinator, Kyle, and his Lanturn.
9 Zoey Vs. May - Sinnoh Wallace Cup Semi-Finals
The Sinnoh Wallace Cup is home to many wonderfully inspiring battles and performance appeals, thus many of the entries will be from that arc of the Diamond and Pearl: Battle Dimension series.
However, Zoey vs. May, on a technical level, is the first most competent contest battle the viewer sees in the Sinnoh series. May's know-how from her Hoenn and Johto contests and Zoey's near-prodigious level of talent as a coordinator is a treat to watch in the early days of the series.
8 Drew Vs. Solidad - Passing Mention
This fight has never been televised, and Solidad in general is a mystery to the viewer and to our central characters. Despite this, fans end up hearing interesting things from Drew, May's rival, about this particular fight.
Solidad won against Drew in his first-ever contest, and Drew admits to crying after his loss against her. While this is only ever mentioned, it is astounding to hear something like that about the ever-confident and arrogant Drew.
7 May Vs. Dawn - The Sinnoh Wallace Cup Finals
When it comes to "long-time coming" wins, this one truly takes the cake. The Wallace Cup final battle that took place between May and Dawn was a true spectacle to witness, not just for the viewer, but for Dawn as well.
Glaceon and Piplup were good choices on either side, and Dawn seemed to have used the doses of humility she received to her advantage. Although she won against May, the fight was one of the closest of the series, only beaten by a few others on this list.
6 May Vs. Drew - Slateport Contest Battle
Drew is cocky, arrogant, and oftentimes he's rather rude to May. But very little of his confidence is unearned, and that makes him a great rival for the viewer's more sympathetic favorite in May. Although May lost the match, she took home a standing ovation, and her parents' adoration and support. And despite Drew's win, the crowd was more enthralled by May's performance than his!
5 Dawn Vs. Lila - Celestic Town Contest
This was another well-deserved win on Dawn's part, but the fight had way more punch than expected. Lila was Dawn's mother's rival.
Joanna, Dawn's mother, was a top coordinator in her heyday and the one opponent she couldn't beat was Lila. It is truly a beautiful moment to see Dawn settle her mother's score and add a third ribbon in her own journey to becoming top coordinator!
4 Dawn Vs. Zoey - Their First Encounter
Zoey serves as one of the main rivals for Dawn in the Diamond and Pearl installment of the Pokemon series. She is also a prodigy when it comes to contest appeals and battles, and as such is a tough rival for Dawn to beat.
Their first battle ends with a total loss for Dawn, and at this stage, she's still a naive young girl who has to face up to her dreams being challenged during her first attempt at a ribbon. The narrative background that sets up this fight is this coming-of-age epiphanic moment for Dawn, therefore her loss is not as disappointing to the viewer.
3 Ursula Vs. Dawn - The Daybreak Town Double Performance
Dawn faced off against Ursula in the Daybreak town contest, and this was the first time that Dawn was successful in a double performance and in a double battle.
Ursula's Plusle and Minun faced off against Dawn's Mamoswine and Cyndaquil. This was a real struggle for Dawn, and even though she won, she knew she had a lot to work on with respect to double performances. However, it's always nice to see an uptight and downright mean person get their just comeuppance, and thus, this ranks as one of the best contest battles of all time.
2 Dawn Vs. Zoey - Finals of The Sinnoh Grand Festival
This contest battle is truly one for the history books and is up there with the best overall battles in the Pokemon anime. Dawn facing off against her rival in the finals, just as they promised each other, is a truly wonderful moment and is on par with Ash's victory against Paul.
Despite Dawn's loss in the final stage, it was an incredibly close battle, and she came as close to beating Zoey as she could. Both had their trump cards in Gallade and Togekiss, and neither backed down until the last second. In the end, Zoey always had the edge over Dawn, and Dawn just fell short by the slightest margin.
1 Nando Vs. Zoey - Semifinals Of The Sinnoh Grand Festival
It is ever so rare that the battles between side characters show up on top of a list such as this. Nando versus Zoey is an example of perfect contest battling.
The battle had everything: finesse in technique, perfect combination moves, harmony between pokemon and trainer, and on-the-fly thinking to get the better of one's opponent. It was such a well-done battle that even Fantina, one of the guest judges of honor, decided to describe both of them as "the greatest."