A lot of strategy games fit this bill to me. Mainly the Paradox ones like Europa Universalis or Crusader Kings. I’d much rather play the most recent version (EU4 and CK3). However, it’s interesting that I feel the exact opposite about the Total War and Civilization Series, where I’ll prefer the original Rome Total War and Shogun 2 Total War over many of the more-recent games, as well as Civ V over VI and VII (though I haven’t played VII yet, to be fair).

The Football Manager series also comes to mind. There’s little tweaks and improvements each year (this year being an exception where they are redesigning the entire engine) so I prefer playing the most recent one (even if I still boot up a few of the older games for some nostalgia every now and then).