1999 Harley-Davidson FLHTCUI Ultra Classic Electra Glide 1450 Twin Cam 88 – £5,495

A Proper Old-School Harley Touring Flagship

There are some motorcycles where mileage only tells a very small part of the story, and this 1999 Harley-Davidson FLHTCUI Ultra Classic Electra Glide is a perfect example.

Now 27 years old, it has covered 54,753 miles from new, but one look around this bike tells you that it has been used, maintained and genuinely cared for rather than simply neglected with age. It presents remarkably well for a heavyweight touring Harley of this vintage and, importantly, comes with useful maintenance history including attention to one of the key areas knowledgeable Twin Cam buyers will want to ask about.

Finished in a gorgeous deep metallic burgundy/red with contrasting fine pinstriping, surrounded by acres of traditional Harley chrome, it has exactly the presence an Ultra Classic should have.

And at £5,495, it represents an enormous amount of proper Harley-Davidson for the money.

An Important Chapter in Harley-Davidson History

The Electra Glide name has been part of Harley-Davidson history since 1965, when electric starting arrived on the company’s big FL touring motorcycle. The famous fork-mounted “Batwing” fairing followed and became one of the most instantly recognisable shapes in American motorcycling.

The increasingly luxurious Electra Glide eventually developed into the Ultra Classic, introduced in 1989 as Harley-Davidson’s full-dress, long-distance touring flagship. Electronic fuel injection first appeared on the Ultra Classic in 1995, another significant step in the development of Harley’s Touring family.

Then came 1999 – a landmark year for Harley-Davidson.

This was the year the famous 1340cc Evolution Big Twin gave way to the new Twin Cam 88 in Harley’s Touring and Dyna families. Displacing 1,449cc / 88 cubic inches, the new engine retained the unmistakable air-cooled, 45-degree pushrod V-twin character that Harley owners wanted, but underneath it was a substantially redesigned powerplant using two camshafts, revised heads and increased cooling capacity.

The FLHTCUI designation identifies this as the fuel-injected Ultra Classic, sitting right at the top of Harley-Davidson’s Touring range. Power is delivered through the traditional five-speed gearbox and belt final drive, making these early Twin Cam touring bikes wonderfully mechanical and characterful machines to ride.

This Particular Ultra Classic

What immediately impressed us about this bike is just how well it has survived.

The metallic paintwork still has a lovely depth and shine, the pinstriping and period detailing suit the bike beautifully, and all of the substantial touring bodywork remains remarkably presentable.

It is also extremely well equipped, as you would expect from Harley’s flagship tourer.

• 54,753 miles from new
• 1450cc / 88ci fuel-injected Twin Cam 88
• Five-speed transmission
• Cobra exhaust pipes
• Full Batwing touring fairing and screen
• Auxiliary front driving lights
• Full fairing-mounted instrumentation and original-style audio system
• Colour-coded hard panniers with chrome protective rails
• Large colour-coded Tour-Pak
• Luxury passenger backrest and touring accommodation
• Tour-Pak chrome luggage rack
• Fairing lowers
• Rider and passenger footboards
• Heel-and-toe gear change
• Extensive Harley-Davidson chrome detailing
• Good tyres
• April 2026 MOT with ZERO advisories
• Substantial service history
• Cam-chain tensioners replaced twice during its life
• Personally road tested by us for approximately 15 miles

The Cobra pipes finish the bike off particularly well, giving the Twin Cam motor the deeper exhaust note a big Harley deserves without detracting from the traditional appearance of the machine.

Some Very Reassuring Maintenance History

This is probably one of the most important parts of the bike’s story.

It comes with a substantial stack of paperwork covering 2017 through to 2021, showing five services during that period.

Included within that history is replacement of the cam-chain tensioners at approximately 25,000 miles.

For anybody familiar with the earlier Twin Cam 88 engine, this is particularly worthwhile information. The original cam-chain tensioning arrangement is an area that sensible owners inspect and maintain as mileage increases.

Even better, the gentleman we took this motorcycle in part exchange from subsequently carried out his own maintenance and advised us that the cam-chain tensioners were replaced again at approximately 50,000 miles.

So rather than simply having an old invoice showing that they were attended to many years ago, this bike has had them dealt with twice, with the most recent work only around 4,750 miles ago.

That is exactly the sort of ownership history we like to hear on a motorcycle of this age.

Condition – Genuinely Impressive for 27 Years Old

We don’t believe in pretending that a 27-year-old, 54,000-mile motorcycle is brand new, and nor should anybody expect it to be.

There are inevitably some age-related marks and blemishes, and there is some minor chrome deterioration/peeling in places when you look closely.

But viewed as a complete motorcycle, it presents exceptionally well for its age.

The paintwork in particular still looks fantastic, the luggage and touring bodywork remain very smart, the seat and passenger accommodation have survived well and there is an abundance of bright chrome throughout the bike.

We have deliberately taken plenty of detailed photographs so you can see the motorcycle properly rather than hiding anything with carefully selected angles. Please study the photographs and watch the accompanying walk-around video – we think the condition speaks for itself.

How Does It Ride?

Before offering the bike for sale, we took it out for a road test of approximately 15 miles.

Everything performed exactly as we would expect.

The big Twin Cam settles into that unmistakable Harley rhythm, the gearbox operates as it should, the bike pulls strongly and comfortably through the gears and, once rolling, it reminds you exactly what these Ultra Classics were built to do.

They are substantial motorcycles at a standstill, but get one out onto an open road and the weight disappears surprisingly quickly. The comfortable riding position, weather protection, huge luggage capacity and relaxed engine make the Ultra Classic a motorcycle designed to cover serious distances.

This one feels like a motorcycle that has actually been ridden and maintained, rather than one which has spent years deteriorating through lack of use.

A Huge Amount of Harley for £5,495

This isn’t being marketed as a concours museum piece.

Instead, it is something we arguably prefer: a genuine, honest, well-maintained old Harley-Davidson that you can actually get on and enjoy.

It has useful history, sensible maintenance behind it, good tyres, an advisory-free MOT, the important cam-chain tensioner work has been carried out twice, it rides exactly as it should and visually it remains a seriously impressive motorcycle.

Add in the fact that this is a first-year Twin Cam 88 Ultra Classic, from an important period in Harley-Davidson history, and there is a great deal to like.

For £5,495, you are buying a proper fuel-injected, 1450cc Harley-Davidson full-dress tourer complete with hard luggage, Tour-Pak, full fairing, Cobra pipes and enormous road presence.

1999 Harley-Davidson FLHTCUI Ultra Classic Electra Glide
1450cc Twin Cam 88
54,753 miles
MOT April 2026 – Zero Advisories
Cobra Pipes
Excellent Maintenance History
£5,495

Take a good look through the photographs, watch the full walk-around video and, if you’re after a genuine old-school Harley tourer with plenty of life left in it, this one is very difficult to ignore.