Hurt & Heal, with a twist!

Houndoom is overrated.

Weavile (Dark): 26
Gyarados (Flying): 76
Houndoom (Fire): 43
Gengar (Ghost): 75
Dugtrio (Ground): 78
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
We can always heal one guy that we both agree to win so we can eliminate the other guys quicker.

Weavile (Dark): 24
Gyarados (Flying): 78
Houndoom (Fire): 43
Gengar (Ghost): 75
Dugtrio (Ground): 78
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Personally, I like Gengar the most.

Weavile (Dark): 24
Gyarados (Flying): 78
Houndoom (Fire): 41
Gengar (Ghost): 77
Dugtrio (Ground): 78
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 22
Gyarados (Flying): 78
Houndoom (Fire): 41
Gengar (Ghost): 79
Dugtrio (Ground): 78
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
For me, it's Gengar > Gyarados > Dugtrio > Weavile > Dragonite > Houndoom

I'd be happy if any of the first three won.

Weavile (Dark): 20
Gyarados (Flying): 78
Houndoom (Fire): 41
Gengar (Ghost): 81
Dugtrio (Ground): 78
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 18
Gyarados (Flying): 78
Houndoom (Fire): 41
Gengar (Ghost): 81
Dugtrio (Ground): 80
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 16
Gyarados (Flying): 78
Houndoom (Fire): 41
Gengar (Ghost): 83
Dugtrio (Ground): 80
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Just evening out these two numbers.

Weavile (Dark): 16
Gyarados (Flying): 78
Houndoom (Fire): 40
Gengar (Ghost): 84
Dugtrio (Ground): 80
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 14
Gyarados (Flying): 80
Houndoom (Fire): 40
Gengar (Ghost): 84
Dugtrio (Ground): 80
Dragonite (Dragon): 28

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 14
Gyarados (Flying): 82
Houndoom (Fire): 40
Gengar (Ghost): 84
Dugtrio (Ground): 80
Dragonite (Dragon): 26

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)
 
Weavile (Dark): 12
Gyarados (Flying): 84
Houndoom (Fire): 40
Gengar (Ghost): 84
Dugtrio (Ground): 80
Dragonite (Dragon): 26

Fainted:
Sharpedo (Water)
Heracross (Fighting)
Starmie (Psychic)
Toxicroak (Poison)
Breloom (Grass)
Froslass (Ice)
Miltank (Normal)
Yanmega (Bug)
Skarmory (Steel)
Rampardos (Rock)
Electivire (Electric)