The ability to achieve high molecular weight poly(ether ketone)s from the polycondensation of bis(aryl chloride)s with bis(phenolate)s has not been consistently demonstrated. The polymerizations presented here help to delineate for specific bis(aryl chloride)/bisphenolate pairs the reaction conditions required to obtain high molecular weight polymers. Polycondensation of 1,3-bis(4-chlorobenzoyl)-5-tert-butylbenzene (6) and 2,2’-bis(4-chlorobenzoyl)-biphenyl (15) with various bisphenolates as well as of 2,2’-bis(4-hydroxyphenoxy)biphenyl(33) with 4,4’-dichlorobenzophenone (41) and 1,3-bis(4-chlorobenzoyl)benzene (43) were used as representative model systems to select reaction conditions that led to high molecular weight polymers.