Mytek Digital Brooklyn Bridge II Roon Core preamplifier
That wasn't streaming exactly, or not in the current sense, because the files needed to be downloaded, stored locally, then either played out of a computer or loaded onto a portable player, but from that point forward it was a steady march to the streaming-dominated present.
Never mind Napsterthe first subscription audio "streaming" service was one you probably wouldn't think of: Audible, the audio book service now owned by Amazon, which started up in 1995. I did beta testing and editing work for early-days Audible, and around that time, I started loading up home-ripped MP3 files on a pocket-sized Rio MP3 player (which by then had replaced Audible's proprietary player), using it in place of a portable CD player. This led to experiments with a PC music library/player running Linux, controlled by a Handspring PalmOS device connected to the stereo system via a Sound Blaster 16 card.