The Afrotropical representatives of the spider genus Cheiracanthium C. L. Koch, 1839 from Madagascar and the Comoros Islands are revised, and new species are described. Five described species are recognized: C. africanum Lessert, 1921, C. furculatum Karsch, 1879, C. insulare (Vinson, 1863), C. leucophaeum Simon, 1896, and C. ludovici Lessert, 1921. The internal genitalia of the female of C. insulare, and the female of C. ludovici, are described for the first time. Thirteen new species, C. ambrense sp. nov. (male female), C. ampijoroa sp. nov. (female), C. andranomay sp. nov. (female), C. anjozorobe sp. nov. (male female), C. ashleyi sp. nov. (male female), C. fisheri sp. nov. (male female), C. foulpointense sp. nov. (male female), C. griswoldi sp. nov. (male female), C. jocquei sp. nov. (male female), C. madagascarense sp. nov. (male female), C. mahajanga sp. nov. (female), C. ransoni sp. nov. (male female) and C. rothi sp. nov. (male female), are described. In most of the endemic Madagascan species the female genital depression is divided by a central septum and the male cymbial apophysis is bent distally.