(1) Background: In addition to conventional magnetic resonance imaging (MRI), diffusion tensor imaging (DTI) has been investigated as a potential diagnostic and predictive tool for patients with degenerative cervical myelopathy (DCM). In this preliminary study, we evaluated the use of quantitative DTI in the clinical practice as a possible measure to correlate with upper limbs function. (2) Methods: A total of 11 patients were enrolled in this prospective observational study. Fractional anisotropy (FA) values was extracted from DTI data before and after surgery using a GE Signa 1.5 T MRI scanner. The Nine-Hole Peg Test and a digital dynamometer were used to measure dexterity and hand strength, respectively. (3) Results: We found a significant increase of FA values after surgery, in particular below the most compressed level (p = 0.044) as well as an improvement in postoperative dexterity and hand strength. Postoperative FA values moderately correlate with hand dexterity (r = 0.4272, R₂ = 0.0735, p = 0.19 for the right hand; r = 0.2087, R₂ = 0.2265, p = 0.53 for the left hand). (4) Conclusion: FA may be used as a marker of myelopathy and could represent a promising diagnostic value in patients affected by DCM. Surgical decompression can improve the clinical outcome of these patients, especially in terms of the control of finger-hand coordination and dexterity.