Background and Aims: The tribe Spermacoceae is essentially a herbaceous Rubiaceae lineage except for some species that can be described as ‘woody’ herbs small shrubs to treelets or lianas. Its sister tribe Knoxieae contains a large number of herbaceous taxa but the number of woody taxa is higher compared to Spermacoceae. The occurrence of herbaceous and woody species within the same group raises the question whether the woody taxa are derived from herbaceous taxa (i.e. secondary woodiness) or whether woodiness represents the ancestral state (i.e. primary woodiness). Microscopic observations of wood anatomy are combined with an independent molecular phylogeny to answer this question. Methods: Observations of wood anatomy of 21 woody Spermacoceae and eight woody Knoxieae species most of them included in a multi-gene molecular phylogeny are carried out using light microscopy. Key Results: Observations of wood anatomy in Spermacoceae support the molecular hypothesis that all the woody species examined are secondary derived. Well-known wood anatomical characters that demonstrate this shift from the herbaceous to the woody habit are the typically flat or decreasing length vs. age curves for vessel elements the abundance of square and upright ray cells or even the (near-) absence of rays. These so-called paedomorphic wood features are also present in the Knoxieae genera Otiophora Otomeria Pentas Pentanisia and Phyllopentas. However the wood structure of the other Knoxieae genera observed (Carphalea Dirichletia and Triainolepis) is typical of primarily woody taxa. Conclusions: In Spermacoceae secondary woodiness has evolved numerous times in strikingly different habitats. In Knoxieae there is a general trend from primary woodiness towards herbaceousness and back to (secondary) woodiness.