Pokemon battles that you wish happened

[Saraneon]

Off the top of my head:

Paul vs Trip
Paul vs Gary
Trip vs Gary (yeah we just went in a cycle lol)
Ash vs Trip (FULL BATTLE IN UNOVA LEAGUE like wth was that when Trip lost in the first round?!)
Iris vs Trip
Cynthia vs Alder
Cynthia vs Tobias
Cynthia vs Bertha (it just makes me slightly off-balance that she's the only Elite Four that hasn't battled Cynthia)
Tobias vs Paul
Wallace vs Steven (the dethroning of Wallace... *cries*)
Alain vs Brandon
Alain vs Cynthia
Dawn vs Paul (just because... Ikarishipping lol)

 

[Redstar45]

REAL Satoshi Vs Shigeru to better match Red vs Green in the canon.
Satosh vs Sakaki a three Times like the games
His match against the Shitennou and A Dragon Master Wataru !
His battle Against Kenta in Mt. Silver

 

[Mythical-Moonlight]

Serena vs Misty (No matter who wins this the Fandom reaction would be totally worth it )

On a more serious level

Leon vs Cynthia could be interesting. Both are Champions that have been undefeated in canon

Also Ash vs Gou though that may occur one day...

 

[DatsRight]

Kiawe vs Lana might have been interesting, both because of their implied rivalry and also because overcoming a full on water type was a roadblock Kiawe still hadn't faced in SM and was even something foreshadowed very early in the series.

 

[Pokegirl Fan~]

Lillie vs Ash in the Alola League finals where Lillie beats Ash and wins the league.

 

[Applecorp]

Kiawe vs Lana might have been interesting, both because of their implied rivalry and also because overcoming a full on water type was a roadblock Kiawe still hadn't faced in SM and was even something foreshadowed very early in the series.

I wouldn't know who to cheer in this scenario because even though I didn't like Lana I also didn't like Kiawe. But who knows maybe seeing a Fire specialist beat a Water specialist would've been cool if Lana had more than just 1 Water type.

 

[RafaSceptile]

Cynthia VS Alder instead of Cynthia VS Caitlin or Alder VS Trip

 

[TheCrazyMaster]

Charizard vs Reshiram
Alain vs Zinnia

 

[Applecorp]

Alain vs Zinnia

That would've been cool to see in the Mega Evolution specials set in the Hoenn region. Too bad those were more about Steven and the weather trio.

 

[Kuzehiko]

Ash vs Cynthia
Tobias vs Cynthia
Alain vs Diantha
Alder vs Cynthia
Ash vs Malva
Paul vs Nando
Paul vs Gary

 

[Applecorp]

Ash vs Cynthia
Tobias vs Cynthia
Alain vs Diantha
Alder vs Cynthia
Ash vs Malva
Paul vs Nando
Paul vs Gary

Thankfully Ash vs Cynthia could still happen because lots of people expect Cynthia to be one of Ash's opponents later in the PWT.

 

[pacman000]

A rematch between Ash & every character he said he'd meet again, but never did.

 

[LadyTriox]

Misty vs dawn

and dawn and may vs Lillie and Serena

blaziken and piplup taking down their teams would just satisfy me haha

 

[Pokegirl Fan~]

Lillie vs Ash in the top 8 of the PWC, it would be amusing to see

 

[ash&charizardfan]

I just want to see a rematch between samurai's metapod and ash's metapod before it evolved.

 

[Decidueye23]

Iris vs Serena.
Iris would be terrified of sylveon lol