Super Bargain vs. Supercar: How Does a 1999 Boxster Compare to a 2018 911 Turbo S?

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1999 Boxster

A 1999 Boxster will lose every race against a 911 Turbo S, but that doesn’t mean it is any less of a Porsche sportscar.

I have recently become the proud owner of a new to me 1999 Boxster. It joins my 2018 911 Turbo S in the garage. The performance capabilities of these two cars are miles apart. However, the prices I paid for these two vehicles are also miles apart. And the enjoyment level and fun factor is a lot closer than you might imagine. In fact, in a number of ways the modest Boxster trumps the mighty Turbo S. We all tend to get caught up in the latest Porsche offerings. Myself included. The Spyder RS is the latest apple of everyone’s eye. The GT4 RS is still hot, the GT3 RS is a magnet for attention. A 911 Dakar will clear the parking lot at a local cars and coffee. The problem is these cars are massively expensive and difficult to get.

Even dropping down to the regular GT models we see inflated prices. Heck, take it down to the GTS range and the prices and markups may not be as outrageous but they still make these expensive purchases. Let’s simplify it even further.

I just went on the Porsche configurator and tried to configure my 1999 Boxster as a 2023 model, and it came out to a little over $80,000. There are no cheap new Porsche sportscars. And looking at the used market doesn’t offer much relief either. Unless of course you are looking at an early 986 Boxster.

They were great sportscars when they were released, and they remain so a quarter century later. In some ways they are even better now as the price to fun ratio can’t be beaten by anything in the modern Porsche range.

My 986 History

986

The 986 Boxster has a special place in my heart. In 2003 I ordered and bought my very first Porsche. It was a Guards Red Boxster. The 2003 had some upgrades from the earlier cars such as a glass rear window and a slight power bump. But it was still a first-generation car, and I loved it.

But I eventually moved on to other Porsche models. From newer Caymans to long hood 911s and eventually to my current 991.2 Turbo S. And as much as I love my Turbo S, I missed the simplicity of the Boxster, and I missed having a manual transmission. When my girlfriend told me that she was finally ready to learn how to drive a stick shift, that was the final straw. The hunt was on for an early Boxster.

1999 Boxster

Garage

I paid a little over $14K for my Ocean Blue Metallic Boxster. Not the greatest deal in the world as you can certainly find these cars for less. But it had only 54,000 miles on it, a clean history, decent service records and was local to me.

It was also well equipped with the sport suspension, sport package, sport design package and sport design wheels. Basically, all the ‘sport’ things you could get in 1999 along with some other goodies. All for not much more than what the Weissach Package alone would cost you on a new GT4 RS. My Boxster also has a manual transmission which is not available for any price on the GT4 RS.

Joe has been obsessed with cars since he got his very first Matchbox toy in the ‘70s. In 2003, he found a new obsession in track days that led to obtaining his SCCA competition license in 2015. In 2019, he became a certified driving instructor for the National Auto Sport Association. His love for all things four wheels has never wavered, whether it's driving some of the best cars in the world on the racetrack, tackling 2,000-mile road trips in 2-seat sports cars or being winched off the side of a mountaintop in a Jeep. Writing for the suite of Internet Brands Auto Communities sites, including Rennlist.com, Ford Truck Enthusiasts, 6 Speed and more allows him to share that knowledge and passion with others.


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