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.)
Either way, I went to my local internet café to download some editing tools for FIFA 99 (to add my beloved Tranmere) and discovered a community (Soccer Gaming) that was incredibly warm and helpful. I still remember Chau Le, who made a lot of those tools and taught me how they worked (so much hexadecimal work).
After many, many months of work (and hundreds of floppy disks being trawled back and forth from my house to the internet café and back), I ended up making and publishing the "English Super Patch (E.S.P.)" for FIFA 99 (after getting dogs' abuse for not releasing it on the date I'd planned to), with kits/graphics by a guy called Kristian Borten.
I was told at the time it was the first ever patch released for a football game, in terms of a massive license-adding graphics-changing package. How true that is I have no idea.
But I've never really stopped being a massive game-modding dweeb since.
* In-fact, the only other game that felt "magic" at the time was Championship Manager, which didn't even use "graphics" beyond text.