Hey batgirl. Not exactly but similar. In the late 80s I use to play Chessmaster in a Commodore 64 computer, which then I updgraded to a Commodore 128. Chessmaster came in floppy and actually flimsy 5.25 inches soft disk. Who knows what version I had and I just remember losing badly to that thing unless I played in the very easy levels. Cheers.
Chessmaster Site

I always remember having to have the Chessmater game to play on the Chessmaster site.
I remember playing correspondence chess when email (for the common folk) was not instantaneous. Email was relayed by BBS's (who remembers those??) and it could take 3 - 5 days to get a response.
But then I only had a 2400 baud modem at the time so ....

My first computer, which I got used, came with CM2000 already installed. It's how I learned to play, along with a book by IA Horowitz.
I'm almost sure that the second incarnation of the Chessmaster site came about upon the release of a version of Chessmaster that enabled people to play together on the internet and that the new site required that players had that version, or that they download some sort of interface.
Rsava, were you a member of IECC? If so, here's a bit of nostalgia: Bits and Pieces.

I played online with Chessmaster while visiting my brother, who played regularly with one friend in a distant town. One Saturday, I played his usual opponent. This was 1989 or 1990. I suspect it was before they had a site. I had Chessmaster 2100 on my home computer, but knew nothing of the internet. My brother is an IT professional.
I started playing online chess in 1998 on Net-Chess.
After Chessmaster X came out, I used it to play online at their site (now run by Ubisoft). It was terrible that users of different editions of Chessmaster could not play each other. Chessmaster was state of the art in the early 1990s, but then gamers took over and it fell behind.
I've used Chessmaster 2100, 3000, 4000, 5000, 5500, 6000, 7000, and tenth edition (or X) as software programs, but only played online with it in that early experience where I understood nothing (but my brother guided me) and with CM X in 2005 or 2006.

Well, 1989-1990 was before anybody had a website. The WWW started in 1992 and the first graphical interface come in 1993, I think it was Mosaic. It wasn't until about 1996 that websites started to proliferate. I remember that I first got online in 1996, using AOL, and, while it seemed pretty amazing, I think my baud rate was 2400bs but soon replaced with 9600/14000bs. There was comparatively little on the web. To begin with, I used the AOL browser, a watered down version of IE, then IE 4.0 and finally upgraded to Netscape Navigator. ICS was a telnet chess site that was around before the WWW and was free. They decided to charge members and changed to ICC. A counter-move to retain a free chess server instigated the volunteer-run FICS. Java, I think, was just becoming common. I'm thinking Yahoo started it's chess site around the late 1990s. Chessmaster's website came about 1996-7 and lasted until about 1998-9, but I could be off with my dates - I just know it came online early on and didn't last very long - but it was exquisite.
I have a hate-hate relationship with chess applications. While their number-crunching has brought us certain things, I feel what we lost is far more valuable. The beauty of chess isn't in the answer, it's in the search.

I had no idea how we were connecting in 1989-1990. My brother and his friend were both IT professionals, and my brother did some development work for ICS in the early years. They may have rigged a telnet connection for Chessmaster that they designed.
I have faint recollections of Mosaic, mostly because my university library embraced it early. I was on the library steering committee, and we spent a lot of time discussion how the role of libraries was on the cusp of major change. As an historian, I urged caution. Manuscripts will always remain vital to historical research. (But, now I use GoogleBooks and the Internet Archive, as well as many university digital collections (https://content.lib.washington.edu/, for instance) so much that I rarely need to put on the white gloves.)

Well, my first browser was text only, in order to "surf the web" you entered a command then entered the # next to the "link". So a page might look like this:
Webpage Title
Dfhfh dfjdfh f hfhdjkhf dhfdhf (1). Fcehjfh kvfkf vhdfvd (2), sdfdfklj nfsd iiedfn jdvkj (3).
My major way of searching the internet for stuff was with Archie, Veronica and Gopher (among others).

I watched a friend stick the part of a telephone you talk and listen with into something that she called a "modem" in 1980. There were several internets long before there was a world wide web.
I have some faint recollection of Gopher, likely from others talking about it, and also because I think our library was using it before they bought into Mosaic.
My experience with CM at my brother's assures me that some connectivity existed with that software before Software Toolworks and UbiSoft got into the act of providing a "site." In any case, CM was never high quality for online play compared to ICS, for example (and ceased being near the cutting edge as software by the time CM 5000 came out).

Yes, Ziryab, libraries would have used mainly Gopher along with the other two (though not as mouch probably).
I remember those telephone modems, never had to use one though.
But as a correction, there was only one "internet", there were several parts of the internet long before the WWW.
Newsgroups, BBSs, ftp, email, WWW and others are all part of the "internet".

I checked with my brother, and he connected via q-link (see Quantum Link at Wikipedia). He remembers some additional software for playing chess, but not that it was Chessmaster. Likely that "memory" of mine is faulty, and stems from the similar look of the board and pieces.
Those were the days when color on a computer screen was a choice between green and amber. Full color were becoming available, as I recall, but these were expensive and unnecessary for chess.
The walnut and maple board with red and white pieces was how CM 3000 (the first Windows version--and now full color monitors had become the norm) looked. As I dredge up memories of the mid-1990s, I have faint recollections of plugging my telephone cord into the back of my computer to look for a game against a human opponent. I do not recall actually playing online before 1998, but I know that my chess software had that capability several years earlier.
I won't quibble over semantics. Suffice it to say that I did not capitalize internets, nor would I. If capitalized, it is always singular.
I'd asked this before a long time ago (in vain), but it came up in a recent discussion, so I thought I'd ask again.
I started playing chess on the web in '96-'97.
I don't think there were all that many chess playing sites around then. I was both computer and internet illiterate at the time and spent most my time trying to figure out how things worked.
The first chess playing site I found and joined was Chessmaster. It was only around for a very short time then disappeared and later re-appeared as part of a larger game site, but it wasn't the same as the original. I think it even required some downloaded program or you had to have a store-bought Chessmaster game or something.
The original site was quite beautiful. I had a 14.4 modem and it took about 3 minutes to load the site. A little blue rectangular counter would appear in the top left corner of the screen indicating how much longer it would take to finish loading. After it loaded, there appeared a walnut and maple board with ornate red and white pieces. There was a chat window, a timer window and a challenge window, I believe. It was quite stunning and waiting for everything to load was a sort of magical experience for me, not something to be dreaded. It was almost like a fanfare before the main event that got my adrenaline flowing.
I didn't do especially well playing on that site. There were some good players, of course, but mostly, I wasn't used to short-timed games as one is apt to play on the internet and, while I've always had trouble with the operational skills, it was more pronounced back then. So, a lot of my poor play was due to non-chess reasons. But, one day, the site just disappeared. The next place I found to play was FICS (the Free Internet ChessServer).
...but that's another story altogether.
Does anyone remember the Chessmaster playing site from the late 1990s?