Want to say Graatch Iukuru were circa 97/98... I know Serafim and Thror were around with Zandorix.. cant remember if Graatch and Iukuru were, but I do remember being in masters with both... in fact no... Iukuru was a little earlier because he got my the skull of a skyflash for my lich quest...
Istendil and Llorenthos I want to say were 95/96... I remember my ap getting ganked down by a 5 man empire gang which llorenthos and istendil were apart of... lost my ice-cold scimitar ;( I loved that sword.
I want to say Challen was around 97 or so too.. I remember him killing me a few times in honorable combat? power.... Think with Zandorix...
hope that helps.