POKEMASTER the Sceptile was my first starter and Pokémon, ever, that I picked in Sapphire. Transferred all the way up to where it's sitting now in AS.
The same as you but with swampert
My first starter was popplio so I guess him
>>31407277
I still have my Heracross I caught in Crystal and my Krookodile I caught in White. Those two are beasts.
>>31407277
my swampert from saphire is still in my X game so i guess thats my oldest one.
cant wait to get it to sun where i plan to abuse the fuck out of the easy berry getting to reapply its evs
>>31407277
the oldest pokemon that I still have is probably the blaziken from my sapphire run, but the oldest pokemon I have and isn't just box bait is the linoone from that run, named Zigzag. One of the few pokemon I've ever got to lv 100 without the missigno item duplication glitch, and he saw play in every generation's postgame up to now thanks to the combination of surf, strength, and pickup.
An empoleon in diamond version now sitting in the ORAS pc
Blastoise from when I started all the way back in gen one. It's living safe and sound in my Pokemon Stadium 2.
Since I couldn't transfer any of my mons from Red and Gold, the oldest I have is my Blaziken from Ruby.
I'm sure my Red version is still somewhere in my room with my original Gen 1 team on it.
But as far as the current games go, I've actually kept all my first game clear teams from each Gen. I still take them out each gen to get new ribbons or something. Obviously the one I've had the longest is my team from Ruby.
Sceptile, Torkoal, Milotic, Swellow, Aggron, and Chimecho.
This Tyranitar came from my first time playing Pokemon Colosseum (which is also my first pokemon game) and was transferred all the way up to gen 6. I even went through the hassle of getting all ribbons you can possibly get.
Except for the wifi ribbon, because JUST.
>>31407277
same as you but with Blaziken