I have 2 clubs that are both pretty old. My putter is a Ping Anser Dalehead I bought new in 1971. I keep it because I putt well with it. if I’m not making putts, it’s not the clubs fault. No reason to change. The other I don’t know how old it is. It might even be older than the Ping. I got it second hand from my father. It’s an Arnold Palmer sand wedge that I started using 50 years ago. I’ve tried the sand wedges that came with the last two sets of irons I bought and I’ve tried 2 Vokey SM-7s, a 56 and a 60 degree but none of those clubs gets me out of the sand better than that old Palmer. It’s got a big, thick, sole that digs down in the sand just the right amount without ever going too deep.
My Nike SQ 3-wood. It's the last original club from my first set I pieced together at play-it-again 5 years ago. I still haven't learned how to hit a 3-wood well enough to be comfortable playing one so I haven't gotten around to replacing it yet. It will be one of the first things I address with lessons this year.
I am honestly not sure of two clubs are chronologically older as got about same time used: 1. Titleist 904 4w with a ProForce shaft I love; and, 2. Scotty Cameron series 62 putter that I get streaky hot with. Both have been in bag at least 7 years and I have tried other 4-5 woods but hard to beat consistent distance and workable nature or look of this old model. I have an older Boca putter I also have played around with but the Cameron had been really good but am considering a change to newer technology.
Both may get changed out this year with putter likely first as I am playing more after a layoff.
My current putter is a Ping Craz-E G2i JDM model...so about 2006 or so. I've tried lots of putters and it's all about feel. This one feels best for now.
Honorable mention to my OG set of Tommy Armour 845s Silver Scots. They still can get the job done and are fun to bring out a few times a year.