Tribe Eucalypteae, commonly known as the Australian eucalypts, is an economical, pharmacological, chemically, and historically important group consisting of over 850 species. These angiosperms are the number one source of hardwood globally with over 200,000 km2 of plantation dedicated to E. globulus. E. grandis and E. robusta, they possess cultural and ethnomedicinal significance, rooted deep in the heritage and culture of the Australian indigenous populations and have acted as sources of biologically active new small molecules in the modern era. The relationship between these plants has been the source of scientific debate and intrigue since the early 1900s, coming to a head in 1995 when the genera Angophora and Corymbia were delineated from the large genus Eucalyptus. The rearrangement of the relative taxonomic rank of these taxa sparked intensive research into the Australian eucalypts, with 86.7 % of the 36,264 publications containing Eucalyptus, Corymbia and Angophora being published since the 1995 taxonomic revision. Despite this large quantity of research, the delineation of these genera remains blurred due to morphological similarities, and ambiguous results from chemotaxonomic studies. Due to this, we have performed the largest chemical investigation of tribe Eucalypteae to date, utilizing a mixture of traditional natural product isolation and discovery methodologies accompanied by modern chemoinformatic analysis, statistical and machine learning investigation of the NMR assignments of published formyl phloroglucinol and [beta]-triketones, and the novel application of non-uniformly sampled HMBC as a chemotaxonomic probe to qualitatively identify the presence of key moieties of chemotaxonomic significance. [...]