This chapter discusses the advantages and challenges of teaching HEL in reverse chronology. Starting with the most recent stages of the language and moving towards the past results in a gradual increase of difficulty throughout a HEL course. Furthermore, irregularities of ModE can be exploited more systematically. On the other hand, external history lends itself less readily to reverse sequencing, which is reflected in the fact that teaching materials for HEL in reverse chronology are scarce. The solution proposed is to teach HEL on the basis of original texts, which serve both as evidence of earlier Englishes and as sources of the historical background. The method outlined is modelled on a CLIL approach taken over from foreign language teaching and provides a more holistic approach to HEL.