well just to add to an old subject. I am one of those people who wanted to know about this because I bought a 2000 Trek 5500 and then went out and gave bigger tires a try and decided to join up to the forum to add to the collection of information.
I have year 2000 56cm 5500 looks like all still stock Dura Ace components of that time. I live by the beach and the paths are fairly well paved but also can get sandy and pavement rough and i wanted something a little bigger than the super speedy thin 23cm tires that come with the 5500.
I was excited to see this white year 2000 pop up for under $600 with a professional tune up. The paint isn't the greatest and the decals are in bad shape, but she still looks nice in pearly white. I like the older components and look or the bike as it is however the 23mm tires are a bit too thin for the riding i do.
I took the plunge and order 700c 28mm tires off eBay - I honestly was just looking at the price no real good research. Part of me thought i was buying tires that would never be ridden because they wouldn't fit my bike.
Vittoria Randonneur II Tire: 700c 28mm Clincher Black Wire - 25/tire so not dirt cheap but not super high end either.
Brought them to the bike shop with the pedals i needed installed and asked them to give it a try. 10 mins later they came back saying the tires fit no problem. Filled to pressure the chain stay still has quite a few mm clearance.
I rode about 30 miles so far so I'll give update closer to 500 miles, right now they work like a charm. I felt a bit more stability over the 23mm for sure. I don't know if anything bigger can fit or if even other 28mm tires will fit, but i am happy with these fit.