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.
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.
ibms docs and help sites suck butt tho.
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.
Do you remember if that was a recent addition?
Full disclosure: I was quite the newbie back then and most of what I "new" about SQL Server was what the more experienced coworkers told me. This was a very IBM-biased place so I'm not surprised they would have stuck to some old shortcoming, like people who still talk about bad MySQL defaults that have been changed for at least 10 years.
Up until that job (which was my second Actual Formal Job), all my DB experience had been with either dBase (I think III plus or IV) and access, so this was a whole new world with me.
It was through MS SQL Server that a colleague taught me about backups and recovery, after I ran an update in prod but forgot to include the where clause ... :)
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).
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.
I don't remember exactly what and why, just that for some specific DML commands another kind of connection was required.
It's notable that 10 was the worst Sybase version, ever.
Source: I worked for Sybase Professional Services from 95 - 99.
It remains one of the most reliable Microsoft products, but few would claim that is a high bar.
I built apps in an active-active bidirectional replication telecom Sybase environment and was deeply involved in migrating it to MS SQL server in the early 2000s. I remember a fair amount of paranoia and effort around the transition as our entire business and customers' phone calls depended on it (for "reasons") but in hindsight it went quite smoothly and there were no regrets afterwards.
The Microsoft went and added a nice BI stack to the whole thing which added a new dimension of value creation at a new low price point.
Starting with version 7.5 it was quite alright, however being Microsoft, it has been mostly used in Microsoft shops, alongside VB, MFC two tier applications, ASP, .NET, Sharepoint, Dynamics,...
