Continuing where I left off, I think I have a decent Classic Sonic game timeline. Most are fine just in release order with the only shifts being due to Metal Sonic being a singular entity and not just multiple hedgehog robots.
Sonic the Hedgehog
Sonic the Hedgehog CD
Tails Adventure
Sonic the Hedgehog 2
Sonic the Hedgehog 3&K (Sonic & Tails story)
Sonic the Hedgehog 3&K (Knuckles story)
Sonic Chaos
Sonic Drift (Chaos GP)
Sonic Spinball
Sonic Labyrinth
Sonic Mania
Sonic Mania Plus
Knuckles Chaotix (birth of Metal Sonic Kai)
Sonic Triple Trouble
Sonic Drift 2 (Chaos GP 2)
Sonic Blast
Sonic R (World Grand Prix)
Tails Skypatrol
Sonic 3d Blast
Sonic the Fighters
Sonic Superstars
Sonic Superstars (Trip's Story and Last Story)
Tails Adventure is the oddball out due to Sonic Origins (he only started flying after meeting Sonic). Also the game gear games run on the logic that there are only six emeralds for some reason. Even post-Sonic 2 games run on this.