>>39204998>elementary school me, ages 4-11 (RSE/FRLG)Eviscerated.
>middle school me, ages 11-13 (DPPt/HGSS)Completely destroyed. When I was 11, I was in a coffee shop playing Diamond, and there was an older kid that was playing Pokemon so I challenged him to a battle. I ended up getting swept by his lead Flygon. It didn't help that I was using terrible stuff like special moves on physical sweepers at the time.
>high school me, ages 13-17 (BW/BW2/XY)Present me would win, but it would be difficult. After getting swept by that guy's Flygon, I went online looking for the answer of my own weakness. Learned about IVs, EVs, type combinations, set ups, and by the time XY had come out, I was one of the best at my school. If anything, my skill in battling has stagnated, since then, since I'm out of practice and 6 years older now.
If anything, it would be similar to when Gary battled Ash, after Gary had already been to the Sinnoh region and got an Electivire. Ash thinks he's hot shit because he has a few Frontier wins, but he still ended up losing.
