early 1990s - A Hercules card I remember but the rest fades in memory.
1997 - S3 Virge 2mb
1997 - Orchid Righteous 3d (3dfx1, awesome microswitch "click!" when the 3d kicked in) - The first time I started GLQuake was probably the most jaw dropping moment of PC gaming for me. Before or since.
1998 Creative Blaster Voodoo 2 (3dfx2) in SLI for 3d.
1998 - Matrox Mystique (2d)
1999-2000(?) Riva TNT2 Ultra (Creative Blaster) (2d and 3d) for that new fangled Quake 3
, kept the Voodoos though.
I now lose track of years but not order -
Geforce 256mb and Voodoo2 SLI
Voodoo 5 5500, used in a secondary machine for a number of years.
Geforce 3 and Voodoo2 SLI
Geforce 4 ti 4200 and Voodoo2 SLI
ATI Radeon 9800 and Pro, finally dropped the Voodoos.
Geforce 5800LX (Secondary machine)
Radeon X800XT
Geforce 6800GTS
Radeon X1800XT
Geforce 8800GTS
ATI Radeon 4870
ATI Radeon 5850
Geforce 670 GTX
2013 - AMD Radeon R9 290
2017 - AMD Radeon RX580
Sometimes ran more than one machine for gaming (dual boxed in Dark Age on Camelot in the early 00's). Contrary to received wisdom of the internet and indeed this forum, I have never had an issue with ATI/AMD drivers, I have found Nvidia drivers much more troublesome (but then again I have never ran Crossfire). The most expensive single card I have ever bought was the Geforce 3 (it's an Asus version with lots of video connectivity, I think it was around £260ish, I could be wrong).
I only swapped out the R9 290 (it's an MSI Gaming version, allegedly quiet) as I got what I can only presume was a misprice on another site for the RX580 8GB (c.£102), it does seem to run noticeably faster but not by much, but it does run a helluva lot quieter when under load (Sapphire Pure RX580)!
PS. The Voodoo 5 and Voodoo2s are still boxed and in my loft, waiting for I don't know what...