If, like me, you don't have a second controller for your Xbox One or Series X, you may think that you wouldn't be able to get this achievement - however I have discovered a workaround using a PC, using a wired 360 controller as your second controller.
Plug your Xbox One controller and wired 360 controller into your PC via USB (this should also work with 3rd party controllers, PS4 controllers etc, though I haven't tested it). Then turn on your Xbox One.
Follow the instructions here: https://support.microsoft.com/en-us/windows/stream-games-fro...
to connect your console and start streaming. You should now be able to control the xbox through the controllers connected to your PC.
Boot up PES, go to Versus under Kick Off. I pressed A to get to the controller select (home/away) screen, and if I recall I had to press start on my second controller to get it up in the game. It prompted me to sign in.
Once this is done, you're all set! Just start the match and play it out. The achievement should pop for both players when you load back to the menus after the game.