This post could end up being a massively difficult task, because there are so many moving parts to a bike’s drivetrain. Ten and eleven speed road groupsets were easy for older bike frames (steel and carbon fiber – aluminum not so much). I’ll stick to what I know, which is admittedly little.
The Ultegra shifters on my 9-speed triple went first. I tried to find replacement shifters to no avail, but I did find a small company new in the drivetrain component market called MicroShift. They made Shimano 9-speed compatible integrated (road) shifters… in a triple, that were priced well and worked as good or better than the original shifters had for a couple of years. Good enough I’d have been fine to keep the bike as it was… until a friend sold me a gently used Ultegra 10-speed groupset that I could use on my Venge. That freed up the 105 10-speed groupset for my Trek.

My ’99 Trek 5200 Triple fitted out with MicroShift’s finest.
The Shimano 105 upgrade – 1999 Ultegra to 2013 105 is a massive leap in technology and a decent drop in weight – was going to be a game changer, but I had to change a lot to make it happen. Here’s how the bike sits today:

So, the crankset is a low-end Shimano. It’s much the same tech as a 105 or Ultegra crankset, just a little heavier. I needed a new English threaded bottom bracket (BBR-60 if memory serves, but I’ll find out for sure and update the post as soon as the shop opens). The crank fits perfectly with no shims to that bottom bracket. That bottom bracket change did lead to the need for a shim change to the cassette at the rear wheel, though. The 11-speed wheel requires a shim to get to 9 or 10 speed… but I needed another to force the cassette out a little further so the chain line worked with the new crankset and bottom bracket, to get the front shifting matched up with the cassette.
There was another massive issue that required a little fabrication trickery. The front derailleur clip for the frame wouldn’t allow the front derailleur cage to drop far enough to work well with the 50/34 chainrings (52-36 worked but had a cadence hole with an 11-28 cassette that I absolutely hated between 18 & 22-mph). Finding a new clip that’ll work with a compact crank and fits a Trek 5500/5200 frame is impossible, so our shop owner welded a bit onto the bottom of my original clip and drilled out the hole (elongating it) so I could get an extra 2 to 3-mm worth of drop to the derailleur cage. That fixed the shifting and the smaller compact crankset worked fantastically.
The final issue I had to deal with was difficult to figure out. I had some chain-drop issues with the small chainring because I was using aftermarket “Amazon” SRAM labeled chainrings. That issue could only be resolved by installing Shimano 105 110-BCD 5-hole chainrings. With the aftermarket chainrings, once in a while, under climbing power, the chain would drop into the bottom bracket for no apparent reason. The problem was the cheap aftermarket chainrings. I believe they worked fine new, but probably needed to be replaced every couple of years – more often than I wanted to bother with. The true Shimano 105 chainrings fixed that issue completely, though.
Other than those solvable issues, everything was bolt-on and simple and I went from a 52-42-30 triple with an 11-26 9-speed cassette to a 50-34 double with an 11-28 cassette.
With those issues corrected, ten or eleven speed will work just fine on my 5200. I’ve heard we may get into trouble with 12, though. That’ll be a post for another day. In the meantime, my old Trek 5200 is riding like a new, much lighter, vastly more enjoyable bike.
The only question left is, should update a classic bike like that? Well, that answer depends in how you want to ride the bike and how long you’re willing to wait for replacement parts when something goes bad. Me? I’d rather ride my bike. Lots. So the change made sense.
This is the opposite to sawing off the legs of a table. 😉
Dear God, I hope so! LOL!
I didn’t know you had done so many mods to that bike.
I had the cadence hole issue with a 105 -9 speed gearset, so I sold the bike in the end and got another one. I now have a 105 -10 speed.
I toyed around with EVERYTHING on that bike to make it exactly what I want. The only original parts are the frame, fork and chainring bolts. Heck, the Venge is almost as extensively changed now that I think of it!
😊
Currently all Shimano 12-speed groupsets are electronic and disc-brake only, so it’s a no go for these older frames anyway.
Interesting! Incidentally, the new tandem has mechanical Ultegra 11-speed… 50/34 & 11-42 for the cassette.