Has any of you tried to run games bought from GOG on a Windows 98SE machine? Any success? I am obviously talking about games which originally supported W98.

I have read of people having some success with it, though I have not tried it myself (as I don't currently have a Win98 machine, or any Windows machine for that matter).

You'll need to install the game on a more modern system first, as I believe the installer only runs on XP and newer. After that though, you may have some success simply copying the installed files. (For some you may have to copy registry values too.)

DOS games where GOG utilise DOSBox's image mounting function will probably not work unless you burn said image to a disc.

I doubt they would work.

No, but it's likely possible with many 90s games and older however you wouldn't be able to use Galaxy, and you'd have to probably extract the games from the installer package using a 3rd party utility (innoextract? something like that IIRC), then you'd have to spend time and effort to manually install the game files and copy them around, possibly muck with the registry, and probably have to do a bunch of other manual hacks. I doubt it would be terribly fun or exciting unless one is really into hardcore mucking with games like that for the purposes of playing them on nostalgic ancient hardware/OS.

So probably possible, but may or may not work with a particular game. Some games may have had to be modified to run on newer OS/systems and the changes might potentially cause the game to not work on older hardawre/OS that are unsupported by GOG for example. Most DOSbox stuff probably works with tweaking I imagine though.

You definitely will not get a point and click and play experience though, it would take some monumental effort. Probably end up taking more time to get a game to run than spent playing it. Getting it to work ends up becoming the game. :)

Why do you ask? I am interested in your situation.

I was wondering the same, but then there are some problematic GOG games that probably work better on some ancient PC, e.g. Interstate '76.

I am not using the trojan horse to drm land, I am sorry, I meant Galaxy. I use the download offline files.

As to why, because it is (will be) there. :)

Interstate mainly needs an old (i.e. SLOW) PC, the OS isn't that important.

Yep, tha's why I said "ancient PC", not "ancient Windows". :)

Usually it just so happens that those ancient PCs are also fit to run only something like Windows 9x or XP at best.

Actually when I just started using Gog I had a working Win98Se machine* and was under the impression Gog offers tweaked versions,
But the original unmodified versions should always be accessible within the game files or at least in the extras.
At the time I always thought the support for new systems was a feature, but everything can run best on the original systems.
It was quite a shock for me to realize many titles are broken on legacy hardware, missing configuration tools and files in general, and I always hoped this would stop being an issue over time as Gog Re-Add missing parts as extras due to popular demand.
Unfortunately, It doesn't seem to be that much of a popular demand after all, and even though there are some wishlists and threads in the game specific forums, Gog doesn't seem to bother about it.
(While it should have been a non issue, maybe Gog fears costumers asking for support on running titles on Win98se and prior?)
But... unless your morals (or fear of viruses,whatnot) overcome you, I believe you can always find the missing parts of titles you own on Gog in their original glory throughout the web... some passionate about it have provided guides you can find.
The thing is, even if it's doable, as some have mentioned before the added value is marginal (unless your legacy hardware is impressive like having an actual Roland - I wish I had that!) in comparison to just run it as it is on Win7.

* I still have it actually - It is a Win 2000 system, that has a boot menu to allows booting into previous Win98Se, which in turn has the ability (through its boot menu) to go back into Old Dos 6.22 with a Dos Navigator shell. but I hardly ever boot it.

Given the context of the thread I just wanted to highlight that fact ;)
Installing Win98 as a secondary OS on your PC won't be a magical solution (if it even works).

Most of the software incompatibilities between Win98 and newer windows version can be fixed/worked around quite successfully. Not sure the trouble of a different PC and dealing with Win98 is worth it.

Though the fun of just trying to do it and fiddle around with things might be worth enough itself for some people ;)
Personally I think puzzling out how to fix the game in question is even more fun.

I did it a number of times: first installing games on XP and then moving files / registry entries to the Win98 SE machine. The biggest problem was locating appropriate registry entries (I was using Total Uninstall for that purpose). Lots of fuss...Not much sense.

Still I think it would be great to have vanilla installers in extras of GOG games.

I think the reason for it is that the customer demand and market for the old games being supplied in a manner that can be both installed on old original computers and actually supported by GOG, is very small and highly niche. The publishers likely would have to agree to their games being provided in an older format like that also and any overhead it may put on them. For GOG to offer something up like that, it they would have to commit to supporting it too and not just throw it out there as-is because it would deviate from the store policy on support. Support staff would have to have training and materials on supporting these games on ancient operating systems and hardware and GOG would have to stock their labs with PCs going back possibly to the 1980s.

From a business perspective there is just no real incentive to do that for the presumed extremely small number of people who would want that and the amount of money it would bring in over and above the current sales of those games. Even if someone was to suggest that they just include floppy disk or ISO images of the original disks as-is, there are many many variations of old games like that, and one person would want the 1st edition, another the patched up release that came out 6 months later, another the special German edition - no not that one the OTHER german edition, etc. Many games had copy protection back then which required all sorts of special circle cards or other physical objects that came in the box to play and would be considered historical DRM also. GOG would either have to ship them as-is DRM-included, or to spend engineering man hours removing or circumventing these things and remastering the old disks and they may no longer run on the old systems anymore.

I understand why some people have a nostalgic desire for these things but IMHO it is neither technically nor financially feasible for GOG to put the time and resources into trying to do something like that. They're already stretched quite thin with their existing resources as it is, with everyone constantly hounding them as to why it takes so long to have certain changes made to the website or Galaxy, etc. so further stretching their resources to try to provide something like this for an extremely small niche of people that would not likely draw in enough money to pay for all of the manpower resources to make it happen properly most likely results in lack of business incentive to do so.

GOG is big in the sense that they're more successful than most other stores that are small and could be considered competition of sorts, but they're small compared to Steam for example. It looks like overall GOG may get maybe 1-3% or less of the market compared to Steam. If you look at Steam's stats for hardware and software usage and look at what operating systems people are using, Windows XP usage is extremely small at this point and support for XP is being dropped by most game companies coming out with new games these days. New games being added in the future that are old games brought back to market most likely will state support only for OSs that are currently supported by the vendor (Microsoft) likely also. When we look and see XP having only 1% or a few % of people out there using it showing up in the stats, we can only guess how many orders of magnitude smaller it is for people still using Windows 98 or Windows 95 or old DOS on 20 year old PCs.

So my take on all of this is that the reason people are unlikely to see GOG or anyone else sell old games in a manner that can be installed and played directly on old computers with old operating systems from the 90s, is simply that for the manpower effort it would take to put supportable products on the market to do this, there is no financially viable sustainable market to act as incentive for a company to do this in 2016. The manpower that could be dedicated to trying to do that would result in much more profit reallocated to bringing products to market that there is a demand for by 99.9% of the marketplace running modern operating systems.

TL;DR version: Profit margins for doing what is being asked would be negligible at best if not more likely negative (a loss) due to the overhead that may or may not be obvious, and those resources are better spent on concentrating effort where the actual wider marketplace is spending money.

Wine's winapi implementation is capable to remap any Windows version. Its win9x implementation is pretty complete.
Thus, yes, I have somewhat used Windows 98 SE via Wine on titles like Shogo. I remember original Windows 98 SE and I am sure not looking back.