I was thinking about this recently, and, seeing as there was no thread for this unusual practice, I decided to start one.
Simple. Have you ever took part in a mirror match?
This means, with the exact same species of Pokemon in the team as your opponent. Not only in Wi-Fi, but you could have also challenged an in-game opponent, such as a Gym Leader, Elite Four or Champion, doing this. Lastly, was it coincidental or intentional?
For the other question, it's similar, and it can expand to any canon. Have you ever imitated the team of a character from the anime or any manga of Pokemon? Have you done an entire game run with it?
Well, in my case, I'm close to doing both of this, but not yet at full. I have five out of six of Shirona/Cynthia's Pokemon in Platinum, excepting for Spiritomb, which, once I get my hands on a shiny one and train it, I'm challenging her to a mirror match. Will probably do this with Adeku/Alder too in Black.
I also have two (shiny) Scizor and a Ninjask, which those who have seen the 13th movie will probably recognize the target of my weird imitation. I did not do a full run, though.
I don't know whether this goes in Video Games or World sections due to the canon expansions. I'll keep watching in case it's moved.