Two new species of the Anablepsoides urophthalmus group and three new species of the A. ornatus group, collected in the Brazilian Amazon, are described. Anablepsoides jari, new species, and A. roraima, new species, are the first records of members of the A. urophthalmus group for tributaries of the Amazonas river basin draining the Guiana Shield, but phylogenetic relationships of these species with other taxa are still uncertain. Anablepsoides jari, from the Jari river drainage, is distinguished from congeners by the colour pattern of flank and unpaired fins in males, whereas Anablepsoides roraima, from the Branco river drainage, is distinguished by the spotted pattern of flank in males. Relationships of the three new species of the A. ornatus group, Anablepsoides henschelae, new species, Anablepsoides ottonii, new species, and Anablepsoides gamae, new species, are tentatively inferred upon the basis of derived colour patterns of caudal fin in males, which are also informative to diagnose each new species. Anablepsoides ottonii seems to be closely related to A. ornatus by both sharing a pointed caudal fin in larger specimens and the presence of reddish brown spots on the dorsal portion of the caudal fin in males, whereas A. gamae and A. amanan share a colour pattern of caudal fin in males, unique among aplocheiloids, in which the dorsal portion of the fin is orangish red with dorsal margin white and narrow black outer border. Anablepsoides henschelae is considered as the sister group to all other species of its group by not sharing an apomorphic asymmetrically coloured caudal fin in males.