Dreamcast millennium controller (25yrs) surprisingly functions perfectly. The buttons, joystick and triggers feel great.
PS2 controllers (19yrs) L2 & R2 buttons get stuck when holding it in a certain angle.
Xbox 360 controller (Used) function with a bit of drift on the left analogue stick.
PS3 Urban camo controller (10yrs) is perfect, I use it for my PC using a Mayflash receiver.
PS4 controller (9yrs) works perfectly, I use it for my ps2 slim with 8bitdo receiver.