Fenofibrate is used to treat dyslipidemia, a health condition that could lead to cardiovascular diseases. Fenofibrate is classified as a class II drug by the Biopharmaceutical Classification System due to its high lipophilicity and low solubility in water. The purpose of this work was to enhance the dissolution characteristics of fenofibrate by incorporating it into 2-hydroxylpropyl-β-cyclodextrin fibers for the first time. Single-needle electrospinning was used to prepare the fenofibrate-loaded cyclodextrin fibers. The drug loading was optimized to fulfill the electrospinning conditions and was determined to be a 1:4 drug:cyclodextrin molar ratio. We found dimethylformamide a suitable solvent and were able to prepare bead-free fenofibrate-loaded 2-hydroxylpropyl-β-cyclodextrin fibers with an average diameter of 2.65 ± 0.82 μm. Drug loading was determined to be close to the theoretical value, 97.2%, with the aid of ultraviolet spectroscopy. Differential scanning calorimetry and Fourier transform infrared spectroscopy were used to track the crystalline to amorphous transition of fenofibrate through fiber formation. The dissolution results indicated a 60-fold increase in fenofibrate from the prepared fibers with respect to the micronized active ingredient.