The production of modular scaffolds that allow for the facile spatial localisation of a variety of interchangeable functional groups gives a toolbox of options for tissue engineering. Furthermore, the need to re-engineer a system for each specific application or function is eliminated. A modular scaffold system based on the versatility of the electrospinning processing technique, chemical modification of bioresorbable poly-ε-caprolactone (PCL) and a controlled free radical polymerization technique is proposed. An antifouling surface is prepared by grafting a poly(oligoethylene glycol) bottlebrush (pOEGMA) from a surface initiating group on silicon wafers and electrospun PCL scaffolds. The surface initiated polymerization method provides versatility which allows for wide variety of monomer units to be selected for bespoke scaffolds and tailored to particular applications, including fluorescent labelling. The antifouling ability of the pOEGMA functionalization is explored and characterised with protein and cell assays. The chemical and mechanical stability of the pOEGMA functionalized scaffolds is explored in a simulated physiological environment over 10 weeks. Following which the chemical and material properties are re-characterised and found to be maintained. A dual functional bilayer scaffold with an antifouling, non-cell adhesive surface and an opposing cell-adhesive surface is then produced. The pOEGMA coating provides the antifouling surface whilst the cell adhesive side is prepared by end-functionalizing the PCL with the cyclic cell binding Arg-Gly-Asp-Ser (RGDS) peptide. Spatial control of the functionality through the mat is achieved by sequential electrospinning of the functionalized polymers. The opposing properties of the surfaces are demonstrated through cell culture and florescent labelling to illustrate clear spatial segregation. Gliding surfaces such as those found in the musculoskeletal systems, the tendon for example, are vulnerable to tethering from scarring following surgical and traumatic injury. This scaffold could offer protection from these scars through the control of cellular migration and may lead to improved patient outcomes.