The phylogeny of the Circum-Mediterranean Tipula (Acutipula) maxima species group (Diptera, Tipulidae) is analysed on the basis of 35 morphological characters. Including T. (A.) luctuosa Mannheims, the group comprises 18 species. The subspecies T. (A.) maxima balcanica Vermoolen and T. (A.) transcaucasica latifurca Vermoolen are raised to species rank. The subspecies T. (A.) maxima pseudogigantea Strobl is no longer recognized as a valid taxon. The females of the species T. (A.) cretensis Vermoolen and T. (A.) cypriensis Vermoolen are described for the first time and details of their terminalia are illustrated. A key to the species of the maxima group is presented and their distribution is briefly discussed.