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Inspired by SP. Big Spazz is excluded from this one for obvious reasons 
Mine is a Sweet potato that was brought second hand 4 yrs ago. Still works sort of. I keep meaning to give it away or throw it in the bin, I have even made a replacement for it, but I still like to ride it. It has brought me so much goodness over the years that I can not bring myself to depart with it.
I also have a board styled off a 1970's McCoy with straight edge rails that a mate made about 7 yrs ago. Its super fun in 2-3ft point break type waves but it hardly gets used. I lent it to a mate - who jumped off the rocks at Dee Why and got smashed up and did some board damage. Idiot. Anyway I need to move it on - have fixed all the dings. Still goes well. Free if anyone wants it.
I'll add to this question and what's your newest one?
So the oldest is a close run thing between a 7 ft single egg and my 10ft Tak. I think the Tak wins by about 6months but they are both about 9 years and still get ridden.
The oldest by age is 1964ish Gordon woods. 9'4. It's rideable and watertight but needs a bit of TLC.
The newest is a sumo, about a month.
Oldest is my Pinnacle 12 months old ,newest a evo2 with flatter rocker 3 weeks old.
oldest would have been cw log - a year. it still hasn't sold. why ive got no idea
newest - the brilliant mr puffer five
Oldest clearwater hp longboard, two years I think. Newest will be ready next Wednesday 
Cripes! You boyz don't hang onto em...
My Robert August 9'6" tufflight "what I ride" must be 12yrs old and got ridden constantly till I got the Hot Log. She's got quite a few patches but still goes awesome and I figure my daughter will someday use it to learn. Had the best surf of my life on it so she's a keeper.
But then I also have a South Coast Surf 9'2" that's 15yrs old but she lives at a mates place and still gets surfed a fair bit. Will never sell that one as my boy Tommo and good friend Mezzy both first stood up on her...
Edit: technically I still have my Mike Stewart Mach 7-7 Lid I brought in Waikiki 24yrs ago
My newest is a hard one. One is new but has been surfed the last 6 weeks since it arrived. The other one is second hand and is 6 weeks old but I have still never surfed it as the surf has been absolutely crap.
.
My neighbours a hoarder, he's up to 30...
Me, I'm sentimental and for me if I surf it and love it why change it. I only change of a board doesn't suit my needs.
I mean, I might change the bobsled for a semi-final but otherwise I'm only looking a newbie bcs the current quiver doesn't cover small/slow waves.
I think too I prefer to progress by getting better rather than better equipment... And I can't afford it 
6'8 Rick Jacko Alloy Joy, it has a steel stringer. Had it for 21 years. Survived 4 years living in Margaret River, Great Southern Bombs, 6 weeks Cactus, 9 months around the great ocean road & about 9 years WA mid west. It was my one board quiver for pretty much 15 years. Didn't feel the need for getting a new board, coz I only got new boards when I snapped one & I was surfing good waves with low crowds. Looking back I would have got so much more out of the places I lived if I had a longboard. I can recall so many days with long lines with too many flat sections in between for this board to enjoy. But I was pretty nomadic up until 6 years ago. I've made up for it now with a nice quiver...but anyway, I will never part with this board. Although would have no problem lending it to a grom to learn on, coz its pretty much indestructable 
It's 12 years old and a bit heavy, made to last and well looked after...and a great rider.
Some beautiful boards there boyzzzz.
I must admit, like a good pair of jeans or shoes, they look better with the shine wore off em and a bit of "experience" in em
I had Sam Egan in Newcastle hand shape me a 9" all rounder in 1998, still ride it daily. Newest is a ECS 9' bamboo comp flex, still undecided on it at this stage.
My 6'6 Spider Murphy....I really need to fix the dings on it from last winter....10 years old and still a go to in good waves
