Brock vs Falkner - Brock Wins because his team ment you had to get a Mankey or train up your starter to Lv16 usually unless you were lucky with Bulbasaur.
Misty vs Bugsy - Bugsy because Scyther was a good adversary if you let the battle pan out because of Fury Cutter. Misty's Starmie was just a pain to get past.
Lt. Surge vs Whitney - Whit... Lt. Surge by a landslide what a combination he had Pikachu, Voltorb and Raichu that is still one of the best combinations I've seen for gym leaders.
Erika vs Morty - Morty and Erika are pretty equal. Erika suceeded where so many Grass specialists failed by having a team with two equal powers and a buddy to complete the package. Morty was just so chilled about battling and if I didn't know better he could've been an Ice Gym Leader ok enough with the bad jokes.
Koga vs Chuck vs Janine - Koga is the best out of the three because of the 13 level boost between Erika and himself. Chuck seemed a bit rushed and didn't really have a personality in comparison to the other gym leaders and Janine was an incomplete Gym Leader and shouldn't have been a Gym Leader.
Sabrina vs Jasmine - Jasmine because of the fact that though she had one of the most human personalities throughout the whole series she was able to use on of the least human-like types.
Blaine vs Pryce - Fire vs Ice, Brain vs Brawn. This is a battle that can only be won by one factor Fire is super effective against Ice. So the winner for this category is Blaine but really anyone with an Arcanine in the story automatically wins.
Giovanni vs Clair vs Blue - Blue but just. Clair to be honest was really the opposite of Lance for so many reasons but her arrogance is probably the best reason. Giovanni was cunning becoming a Gym Leader and then covering his past up to become the leader of an "International" crime organization which succeeded where others failed, however Blue conquered all of this by being able to infiltrate said organization while at its peak, become champion "though briefly" and find a living doing something that he enjoyed, battling.