Thanks for your efforts Mavromatis, however I was looking for ISOs and not loose files. Lucky enough a crazy idea paid me off - somehow web.archive.org has exactly one snapshot of the site from 2015 and somehow the files in question got included! If you still have the opportunity to host it - please do, I would expect at least a few people will be grateful for that in the future.
I'll keep the files shared for at least a few weeks in hopes of someone re-hosting it or you can go to the source (look up ttd.bl4ckb0x.de on web.archive.org - though I would't consider it a reliable backup and ATM it's down).
TTD_DOS (Multilanguage, Original CD-ROM ISO, DOS Version) https://mega.nz/#!smhSgT6S!pkxLpNlp8b4- ... kvgb9I-sZA
TTD_WIN95 (Multilanguage, Original CD-ROM ISO, Win95 Version) https://mega.nz/#!EvwjHBIQ!_znRIqBn6c7f ... m8AeDFNaWc
Transport Tycoon + World Editor (Multilanguage, Original CD-ROM ISO) https://mega.nz/#!AuhDHJzC!-UEO2C0lMl6o ... 9yljI9YXP0
Thank you ttd.bl4ckb0x.de!
Best wishes to the TT community and the old skool.