Polymeric brushes provide an attractive functional interface for a variety of applications in materials and biomedical sciences. Facile access to functionalized brushes can be realized through effective postpolymerization functionalization of reactive brushes. Over the past decade, efficient chemical transformations based on various "click" reactions have been employed for functionalization of polymeric brushes. This paper reports the first example of utilization of the Diels-Alder cycloaddition reaction based functionalization strategy that allows efficient conjugation of maleimide-containing molecules onto furan-containing polymer brushes under mild and reagent-free conditions. Polymers incorporating furan groups as side chains are "grafted from" silicon oxide surfaces and investigated toward their functionalization. Brushes are fabricated using atom transfer radical polymerization with varying amounts of furfuryl methacrylate to enable control over extent of functionalization, along with a poly(ethylene glycol) chain containing methacrylate as a comonomer to impart hydrophilic and antibiofouling characteristics. Functionalization of these reactive brushes were investigated through the immobilization of a model compound N-ethylmaleimide, a fluorescent dye BODIPY-maleimide, and a maleimide-containing biotin based ligand to direct the immobilization of streptavidin-coated quantum dots.