I am not good with years, but this is the rough order. Some speakers/systems were overlapped in different systems at the same time, so I'm going off of date of purchase. Of what I remember:
Magnavox boombox
Magnavox 3-in-1 with detachable speakers
(both of the above were from when I was a kid, before 13 years old or so)
"Real" Speakers:
Allison DIY's (this is when I learned I shouldn't DIY

)
JBL 4312A
KEF Coda somethings (short time frame, I just remember they had great mids and very little bass)
JBL L100
Energy E:XL 15, 16, 26 and E:XL-C
Energy A3+2, A2+2 and AC300 (which I bought in 1997 and just gave to my brother last month, great speakers.)
Hales Revelation 3 (I shouldn't have sold these)
AV123 RS250/RSC200/RSS300
AV123 RS450
era D5
PSB Imagine B
Def Tech Mythos STS/9 (quickly replaced with a Mythos 10)/Gem XL
Def Tech CS-8060HD (replaced the Mythos 9 with a ten, and then replaced the Ten with this)
Currently debating SVS Ultra set up or KEF R700 based system
Somewhere in that time I also had Infinity Reference Four's that I lost in a bet, Polk surrounds, something from Koss, something from Advent, and a few other speakers that I remember only by how they looked, which is never a good sign.
Assorted desktop computer speakers
Logitech "stuff"
Audioengine A2
Audyssey Lower East Side
HT Subwoofers:
DIY dual voice coil Pioneer in a 5 ft^3 sealed enclosure
DIY Polk db based sub in a 3 ft^3 enclosure (maybe I didn't really learn not to try DIY as early as I thought...)
M&K S-150 THX
Dual Energy subs: ES-18XL and Microstar 12.1
Dual SVS PB12+ (12.3)
Dual AV123 MFW-15
Dual SVS PB13-Ultra
SVS SB12-Plus (bedroom system, still have the Ultra's in my HT)
Currently debating SVS SB13-Ultra for their smaller size and set up options
Car audio (I don't remember any of the model numbers, but assorted component and subs):
Alpine
Polk
Rockford Fosgate
Rainbow
OZ Audio
JL Audio
and many others, but its been a long time.
Other:
Junk that was installed in the ceilings in my house by the builder.
Grado, Senheiser and Beyerdynamic cans of assorted types. Still love my Grado SR-60i's for rock music!
Man, I've been slacking off.