In this work, we pioneered the preparation of diamond-containing flexible electrodes using 3D printing technology. The herein developed procedure involves a unique integration of boron-doped diamond (BDD) microparticles and multi-walled carbon nanotubes (CNTs) within a flexible polymer, thermoplastic polyurethane (TPU). Initially, the process for the preparation of homogeneous filaments with optimal printability was addressed, leading to the development of two TPU/CNT/BDD composite electrodes with different CNT:BDD weight ratios (1:1 and 1:2), which were benchmarked against a TPU/CNT electrode. Scanning electron microscopy revealed a uniform distribution of conductive fillers within the composite materials with no signs of clustering or aggregation. Notably, increasing the proportion of BDD particles led to a 10-fold improvement in conductivity, from 0.12 S m^-1 for TPU/CNT to 1.2 S m^-1 for TPU/CNT/BDD (1:2). Cyclic voltammetry of the inorganic redox markers, [Ru(NH₃)₆]^3+/2+ and [Fe(CN)₆]^3-/4-, also revealed a reduction in peak-to-peak separation (ΔE_p) with a higher BDD content, indicating enhanced electron transfer kinetics. This was further confirmed by the highest apparent heterogeneous electron transfer rate constants (k⁰_app) of 1 × 10^-3 cm s^-1 obtained for both markers for the TPU/CNT/BDD (1:2) electrode. Additionally, the functionality of the flexible TPU/CNT/BDD electrodes was successfully validated by the electrochemical detection of dopamine, a complex organic molecule, at millimolar concentrations by using differential pulse voltammetry. This proof-of-concept may accelerate development of highly desirable diamond-based flexible devices with customizable geometries and dimensions and pave the way for various applications where flexibility is mandated, such as neuroscience, biomedical fields, health, and food monitoring.