What's the oldest save file you still have in your game?

The content started in late 2016 but I've needed to "save as" a few times. I'm mainly playing one main save at this time. It's easy to get back into it because everything is in there.

I first got the game in 2017 around this time of year. I don't play the save anymore but I like to have it for sentiment.

Mine is from 2015. I got Get To Work and started different saves on each career. I ended up deleting the doctor and detective saves after maxing out the careers, but I still have the scientist save.
My scientist became instantly my favorite Sim and he still is. That save is my favorite, but unfortunately I can't play it as much as I'd like to, anymore, because something is wrong with it. My Sims will start freezing after about an hour of game play and it gets worse until they will freeze completely. When I play my other saves and then return back to my favorite one it works again, but it'll start freezing at some point.
I'm afraid that this save will become completely unplayable soon. I have the same problem with my second oldest save too.

My main game save goes back to 2014. I have many save as’s to that game. Not sure exactly how far back they go without having been deleted, probably pretty far.

I honestly wish I kept ALL my save files from the very beginning when I first started playing The Sims when I was like 10 years old... (I'm 24 now). It would be interesting to see how I've progressed since then to the way I am now. Especially since my building and designing has definitely gotten much better from 14 years ago! lol

I was late to the party and only started playing at 2018, my main save is from that time.

I overwrite and delete my saves regularly. So my current ones are form 2019.

From when I moved: 2016 :)
I don't tend to play with the same save for that long as I create a new one for almost every pack, and I don't tend to delete old saves either :D

I tend to delete saves when they no longer appeal to me, and I have no plans of ever going back to them. I feel like the oldest one is my Westbrook family rotation, which I started not long after Parenthood came out. I'm still playing that save. I took a bit of a break for a while but since DU, I've been playing that one almost exclusively.

I remove all old - add back in the Sims I want from old - then start a new for a new ep. That way never bring trouble with it all. I do eventually get them all back on the same page but bring no problems with them - so far anyway. (Sims 3 is far easier to do this with but it can work in Sims 4 too - be easier if we could have more lots and move sims in their houses like in Sims 3.

Yes keeping good old saves is a must or you tend to lose Simmies so I try not to do that. I copy them back to my library also once new game is activated and going well.