Older Pokémon games you played late?

Didn't play Sword/Shield until a year after release roughly.
Didn't play Let's go Pikachu/Eevee till after that xD
Prob too short to count though =p

For all the previous games I'd usually play them around release. I have picked up some second versions later on though.
For example I started an Ultra Moon playthrough roughly 6 months ago (which I still haven't finished yet) and I bought it around that time too. Did already play/complete Ultra Sun though. Similarly I also played through newly purchased X & AS not long before playing through Sword/Shield even though I already played Y & OR back when they released.
 
Most of them to be honest

Missed Gen 1 and 2 because of age related reasons, although I played Gen 2 much later and it became my favorite.

I played Gen 3 at release, though I was a baby, it was one of my first video games. I remember hitting random buttons on the nickname screen so all of my Pokemon looked like gibberish. Missed Gen 4 because I stuck with Gen 3 for years, then I discovered rom hacks as a child so I had less reason to play anything else. The ones back then were much less 'great' in quality, but they kept me busy. I even tooled around with making my own, but nothing ever came of it.

I was 10 during Black and White's US release. I did not play these until 2018 when I found them cheap in a mall with my own money.

I'm pretty sure it was Gen's 6 and 7 that I played around release. Omega Ruby was a given as a gift, it restored my interest in the franchise. (partially i just found the art style cute).
 
LeafGreen was the first one I went back to - picked it up on the same trip that saw me nab a brand new copy of Platinum not long after it came out (a big regret is that I didn't know it was coming out, so restarted my long-running Diamond save for the car journey and thus lost a bunch of Pokémon from 2005 - now my oldest is only 2011). Given I'd seen original series anime, it was fun to finally get to use all the originals (Gen I 'dragons' - Charizard, Gyarados, Dragonite - have long been my favourites). It still holds up, the simplicity and having actual choices of direction in those and HgSs are refreshing compared to the relative prescriptiveness of the Gen III, IV, and V main games.

I think I picked up Black 2 a couple of years after release - the quick turnaround of HgSs-BW-B2W2 caught me out - but I've only completed it once as it was pre-owned and kept crashing around the time the big ship appears.

Oh, and I had Battle Revolution for Wii a couple years after it came out, which was great fun to see proper 3D battles, although because it was only battling I did tire of it quickly. My parents were very reluctant to get me games though, forcing me to take awful trade-in deals when I wanted a new game, so it and about 6 others collectively got me the latest edition of FIFA that year. Atrocious short-term decision-making, especially for independent business owners!

I doubt I'll ever buy a new Pokémon game now, but I would definitely consider getting XD if it didn't also mean having to track down a GameCube, Shadow Lugia looked so cool!
 
For me it would be Pokemon Black. It was released on 2011 and played Pokemon Black somewhere around 2018-2019.
 
Pokemon Blue on Virtual Console! :D It's so great that they did that. I don't see any way I would have ever gotten to experience gen 1 if it weren't for the VC.

Also, I started playing Black 2 when it first came out, but I guess I hit a slump in my interest in Pokemon for some reason, so I just...never played past, like, Nimbasa City until only a few years ago, actually. Even though I got back into it enough to play X and Omega Ruby. I don't know why I lost interest so thoroughly, either - it's a really good game! 🤷
 
All gens i and ii, of course, and gen III. Most of the spinoffs before gen IV, too. All of those games, I played much later than when they came out because I didn't have a system to play them until...2008, lol.

I got D/P a year into their release, but I got Platinum the day it came out, and for the most part, I've gotten almost all new Pokemon games around the time they come out within a month, or two. Except LGPE I skipped those games entirely. I'll buy them eventually for collection's sake, though, and maybe play through them once.
 
Pretty much everything pre-Gen 4 because I only found out that Pokemon was a game and not just the anime during the late Gen 4/early Gen 5 and these two generations were where I started playing with Soul Silver and Black. First 2 generations I wouldn't be able to play anyways since I was too young when they were new but I missed out on Gen 3 when it was new and only played Gen 3 games for the first time in the Gen 5 era. My first time playing through the Gen 1 and 2 was when they came out on the Virtual Console in 2016 and 2017.

I also missed out on every spin-off Pokemon game because I don't like them that much so I only played Conquest when it was new during Gen 5 but never actually finished it. However I found and got PMD Explorers of Sky for a very cheap price during the summer so I started playing through that very slowly and hopefully I'll finish it until the next summer lol because as I already said I'm not a huge fan of the spin-offs.
 
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I also missed out on every spin-off Pokemon game because I don't like them that much so I only played Conquest when it was new during Gen 5 but never actually finished it. However I found and got PMD Explorers of Sky for a very cheap price during the summer so I started playing through that very slowly and hopefully I'll finish it until the next summer lol because as I already said I'm not a huge fan of the spin-offs.

Oh yeah, Sky is one I want to try eventually too, heard really good things about it. Hope you'll enjoy it yourself! I liked Conquest personally but I can see why it'd not appeal to some people, definitely a veeery different formula aha.
 
I didn't play Pokemon Diamond until 2008. I was a teenager back then and could hardly squeeze out money for other games and I couldn't ask my parents for Pokemon games because they hated Pokemon so much, so it took me a while to get to Pokemon Diamond.

Likewise, I didn't play Pokemon FireRed until 2009.

Now that I think of it, I also didn't play Pokemon Ruby until later, too (Spring of 2003). For many of the same reasons as above, except my parents did buy this one for me, begrudgingly lol.

Oh god, the more I remember, the more I know this has happened many, many times.

I didn't play Pokemon HG until 2011. My DS had broken back in 2009 and so I didn't get to play HG until I got my 3DS in 2011. And I first played Pokemon Black in Spring of 2012 when I got my first job's first paycheck.

The generations beyond that I have played the new games as they came out.
 
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I have played every pokemon title there is at this point, most in which were close to the release date...

However Heart Gold I think was probably my latest. I had lost interest in pokemon and had no knowledge of HGSS. I saw my friend playing it in High School in like December or January and ended up getting it the weekend after. So it was about 2 or 3 months late.

I also never got Platinum for the same reason. I didn't get that game until 2019 and still haven't played the full game because it is just such a hassle to train pokemon in. I also think it is a fake, so I don't know if I should count it or not. But it would be the latest if at all.
 
i've played majority of them on release, but i did play red and silver for the first time during gen 3 so there's that. i technically played yellow first when i was a kid during gen 1, however i lost the cartridge before i beat brock so lol it barely counts. i didn't get another main game until sapphire at release and then i bought red and silver when i was 11 from my bus driver's son for $5 each...crazy to think i got them for that price back then. them being a little older didn't bother me at all tbh, i really enjoyed them and still do to this day. i have never rly had an issue playing games when they're past their prime, it's fun to see how the games play and function and work with what you've got.
 
I'll let you in on a little secret: I haven't played a single Gen I game to completion despite Kanto being one of my favourite regions. Closest experience I've had to that was Let's Go Pikachu, which I bought at release (and have loved ever since).

I did play some of Crystal thanks to emulators around 2009 (right before I played HG/SS), but I never got to actually complete it until 2018 when I bought the VC release on 3DS - and to boot, I did two playthroughs that year! It's one of my favourite Pokémon games now.
 
It took me a good year after the release of HGSS for me to play it. No real reason, I just wasn't in a Pokémon-ing mood when they dropped. I also just got Pokémon GO like a month or two ago and haven't touched it, so I guess I'm super behind and still haven't played it. 。゚(。ノωヽ。)゚。
 
I started with Emerald, then Diamond, both quite soon after release. Got LeafGreen after that. For a quick play through its still a favourite. Despite its 2012 release and my lack of studying during my final school year, I didn't get my hands on Black 2 until 2014, then didn't play it for a year as Assassin's Creed Black Flag got a hold of me. The initial delay makes sense - I spent all my money on an 'expedition' that summer, but I don't get why I didn't get a copy later in 2012. Pre-owned, Black 2 glitched out on the pirate ship and although I appear to have eventually completed it I have no fond memories.
 
I only played X in 2019. Because when Black & White came out in 2011, like many people I wasn't a fan of most new pokémon's designs and of the fact that you couldn't catch any pokémon from the previous generations before the elite 4. So I started losing interest in the modern games. Throughout the 2010s I still played lots of pokémon but exclusively the first four generations (from Red to HeartGold). With the exception of Alpha Sapphire, which I played right when it came out (because I was a big fan of the Hoenn games as a kid) and I wasn't disappointed, I've replayed it multiple times.

And finally in late 2019 I decided to play X and, although I didn't like the fact that the game was way easier than previous generations, I still found it very enjoyable, especially because the Kalos region and the graphics were so beautiful.
 
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