Morphological and molecular data were analyzed using parsimony to trace character evolution within Anagallis s.l., including Anagallis, Asterolinon, Pelletiera, Lysimachia nemorum, and L. serpyllifolia, which are distributed among two sister clades. The first clade, comprising Anagallis arvensis, A. foemina, A. monelli, Asterolinon, Pelletiera, Lysimachia nemorum, and L. serpyllifolia is supported by synapomorphies such as an annual, repeatedly branching habit, sessile leaves, flowers in almost all leaf axils, and membranous slightly dentate calyx margins, of which all but the last are homoplasious within Anagallis s.l.. The second clade, comprising Anagallis species only, is supported by a large number of synapomorphies, of which the majority are floral features. Placement of ten taxa, for which no DNA was available, is proposed based on morphological characters evaluated in the light of the result of the phylogenetic analysis of sequenced taxa.