Polyvinylphosphonates are highly promising candidates for (bio)medical applications as they exhibit a tunable lower critical solution temperature, high biocompatibility of homo- and copolymers, and a broad foundation for post-synthetic modifications. In this work we explored polymer-analogous transformations with statistical polyvinylphosphonates comprising diethyl vinylphosphonate (DEVP) and diallyl vinylphosphonate (DAlVP). The CC double bonds were used as a starting point for a cascade of organic transformations. Initially, the reactive moieties were successfully introduced via bromination, epoxidations with OXONE and mCPBA, or thiol–ene click chemistry with methyl thioglycolate (6). The obtained substrates were then employed in a variety of consecutive reactions depending on the introduced functional motif: (1) the brominated substrates were converted with sodium azide to enable the copper-mediated alkyne–azide coupling with phenylacetylene (1). (2) The epoxides were reacted with sodium azide for an alkyne–azide click coupling with 1 as well as small nucleophilic compounds (phenol (2), benzylamine (3), and 4-amino-2,1,3-benzothiadiazol (4)). Afterwards the non-converted allyl groups were reacted with thiochloesterol (5) to form complex polymer conjugates. (3) An acid-labile hydrazone-linked conjugate was formed in a two-step approach. The polymeric substrates were characterized by NMR, FTIR, and UV/Vis spectroscopy as well as elemental analysis and gel permeation chromatography to monitor the structural changes of the polymeric substrates and to prove the success of these modification approaches.