Researchers interested in the history of the Indo-European family of languages have used a variety of methods to estimate the phylogeny of the family, and have obtained widely differing results. In this paper we explore the reconstructions of Indo-European phylogeny obtained by using the major phylogeny estimation procedures on an existing database for 24 Indo-European languages compiled by linguists Don Ringe and Ann Taylor. Our study finds that the different methods agree in part, but that there also several striking differences. We discuss the reasons for these differences, and make proposals with respect to phylogenetic reconstruction in historical linguistics.