So let's say I take a gym, and I place a CP 100 Charmander to hold it. Then, I do a friendly battle, picking my Pinsir to battle against Charmander. What happens if I win/lose? Is the XP that I gain used to level up my Charmander or increase its CP level? I got an achievement for training 10 Pokémon, but their CP levels are still the same. I don't get how it works.
Pokemon Go – How Does Training Work?
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Best Answer
When you battle against a gym that belongs to your team (training), if you win, you get an XP bonus for yourself, and a Prestige (reputation) bonus for the gym. Enough of the latter and the gym levels up. Higher level gyms can hold more Pokémon (one per trainer), which makes it harder for opposing teams to take over the gym. If you lose against your gym, no bonus for either you or the gym. The Pokémon you initially put in the gym stays there until it's bumped out by the gym losing enough Prestige to drop one or more levels (the lowest CP Pokémon drop off the lower end of the ladder, essentially). The gym loses Prestige by having opposing teams win against it.
If your gym Pokemon is returned to you as a result of the gym losing enough Prestige, your returned Pokemon is returned fainted, with no health, requiring healing via a Revive and Potions before another battle.
In your example, I don't think either of your Pokémon (Charmander left at gym to train, or the Pinsir you bring in to challenge) gain anything (it'd make sense if they did, but I haven't seen it).