Sensible Soccer on my trusty Amiga 600 is the first that I remember, when it was released in 1994.
There was a demo disk that had a "special edition" on - featuring
Norwich vs Man United (the team that Jon Hare of Sensible Software supported, vs everyone's favourite/despised team), but also,
Apples vs Oranges (based on the old English phrase "like comparing apples and oranges", because the developers were silly sausages).
I absolutely loved it, and when playing with friends it was even better - so I had to buy it (and each special edition that followed, e.g. "European Championships Edition", which included updates to the real rules, such as the Backpass Rule).
I loved the gameplay, and loved playing tournaments with friends, but when Sensible World of Soccer launched with a "Manager Mode" (and even player ratings / special attributes that made a real difference), I was absolutely hooked. It took over my life.
I played other games around the time - my friends had PCs and games like Actual Soccer, which was magical graphics-wise. But even 3D graphics couldn't tear me away from SWOS*.
...until my brother-in-law got a PlayStation and invited me over to play ISS Pro Evolution. At that point, my life changed forever.
PES became a religious experience - a much more "serious" game, slower, more grounded, and every input you made translating
absolutely perfectly to what happened on-screen.
(Including what would happen if you tried to make an audacious pass with a donkey of a defender.)
It upset me that there were no lower leagues, no Tranmere Rovers - the database was a fraction of the size of SWOS - but there was no going back after ISS Pro Evo.
(He also had FIFA 98: Road to World Cup, and it just cemented my opinion that FIFA - which I'd tried on a friend's Mega Drive years before - was a "silly" attempt at a football game, but lovely to look at.)
After that, my family bought a PC and I bought FIFA 99, purely because of a rumour at school that if you had a 3DFX Voodoo card, you could play snowy matches. It turned out to be a lie.
(The PC was deemed a better purchase than a PS1 due to having homework applications and more power anyway - so I made the most of it.)