SQL Server 2000 was well received in the segments that mattered as a challenger. Oracle was in first place running on Unix. However, it was viewed as expensive and the procurement experience was regarded as unpleasant. People wanted competition even if they didn't think SQL Server, or another alternative, could unseat Oracle for the most important stuff.

Windows was really picking up steam and there was a move to web development in the Windows-based developer space. Visual Basic and Delphi were popular but desktop development had peaked. ASP was for building your apps and SQL Server was the natural backend. SQL Server fed off this wave. It wasn't dislodging Oracle, but rather than every app being built on Oracle, more apps started to use SQL Server as the backend.

Then ASP.NET appeared on the scene and demand grew even more. It was a well-integrated combo that appealed to a lot of shops. I started my career in a global pharma and there was a split between tech budget. IT was a Windows shop for many reasons and ran as much on SQL Server as possible. R&D was Unix/Linux with Oracle. There was a real battle going on in the .NET vs Java (how about some EJB 1) and the databases followed the growth curves of both rather than competing against each other.

The SQL Slammer worm brought a lot of attention to the product. There were instances running everywhere and IT didn't expect so much adoption. Back then you had a lot more servers running inside offices than you do today. My office was much like my homelab today. This validated the need so the patches got applies, IT got involved in the upkeep, and adoption continued to grow.

Oracle's sales folk and lawyers were horrible to deal with. I had some experience of this directly as they tried pushing Java-related products and my boss dragged me into the evals. One of my in-laws was outside counsel in the IT space doing work with enterprise-sized companies. He claims they are the worst company he's ever had to deal with and wouldn't delegate any decision-making locally which endlessly dragged out deals. They had a good product but felt they could get away with anything. Over time he saw customers run lots of taskforces to chip away Oracle usage. This accelerated with SaaS because you could eliminate the app AND Oracle in one swoop.

I remember talking to one tech leader at the time who described it as "surprisingly good, for a microsoft product" which sort of summed it up. But it had similar characteristics to sybase except more so because you had to run it on an NT server (iirc) and so there was an even harder cap on the scale of hardware you could run it on, whereas you could run oracle on really top-end sparc hardware that was way more powerful than anything that ran windows.

Depends if the director or VP liked Microsoft or not. I’ve worked at places that loved SQL Server and Microsoft server products in general. Others did not use them anywhere in their datacenter and wouldn’t have considered them. Oracle, IBM, and Microsoft were very dependent on if the people in charged liked them. Not so much technical merits.

SQL Server was very good and used in a lot of enterprises. ime the decision between Oracle and SQL Server tended to be down to whether the IT department or company was a "Microsoft Shop" or not. There were a lot of things that came free with SQL Server licenses and it had really nice integrations with other Microsoft enterprise systems software and desktop software.

Oracle was definitely seen as the more mature and resilient (and expensive!) RDBMS in all the years I worked in that space. It also ran on Unix/Linux whereas SQL Server was windows only. Many enterprises didn't like running Microsoft servers, for lots of (usually good) reasons.

MS SQL Server was forked from Sybase in 1993. Not sure how much the code had diverged by 2000. Informix was also a contender back then.

SQL Server was Sybase until (I think) version 4.9, just rebranded as Microsoft SQL Server.

Then the two versions split and I don't think that any of the Sybase source code remains in what is SQL Server today.

That said, a lot of the concepts (like a significant number of system stored procedures) and also TSQL remain almost the same, with small differences (except for system functions, which SQL Server has a lot more functionality).

When you come from the Sybase world getting a start on SQL Server is quite straight forward when it comes to handling the database.

Internals and other low level nuts and bolts differ nowadays, of course.

SQL Server's claim to fame was GUI admin tools making life easier for many who bore DBA responsibilities only in anger.

It remains one of the most reliable Microsoft products, but few would claim that is a high bar.

This is a very short comment on SQL Server's code improvements (post-Sybase).

https://news.ycombinator.com/item?id=18464429

The top comment in the post is a long complaint about the code quality of the Oracle database (worth a read).

My experience at the time was that it was perceived as not serious enough and lacking important features. If my memory isn't very bad, I believe as late as 2000 SQL Server still only supported AFTER triggers.

In my experience in the late 90s and early 00s, besides Oracle and Sybase, DB/2 and Informix were also regarded as good. Oracle was considered the best though.