Lateral epicondylitis of the elbow, commonly known as tennis elbow, is a musculoskeletal disorder characterized by pain and degeneration of the common extensor tendon. Despite various treatments, optimal management remains debated. This study aimed to compare the effectiveness of focal extracorporeal shockwave therapy (F-ESWT) alone versus a combination of focal and radial pressure waves (F-ESWT+R-PW) in treating chronic lateral epicondylitis. This retrospective observational study included 45 patients diagnosed with chronic lateral epicondylitis divided into two groups based on the treatment received: group A (F-ESWT, n = 23) and group B (F-ESWT+R-PW, n = 22). Both groups underwent three weekly sessions of their respective treatments. Patients were also given a home exercise protocol. Primary outcomes were assessed using the Visual Analog Scale (VAS) for pain and the Patient-Rated Tennis Elbow Evaluation (PRTEE) for pain and functional impairment at baseline (T0), 4 weeks (T1), 12 weeks (T2), and 24 weeks (T3) post-treatment. Secondary outcomes included grip strength and ultrasonographic measurements of common extensor tendon (CET) thickness and vascularization. Significant improvements in VAS and PRTEE scores were observed in both groups at all follow-up points. Group B showed greater pain reduction at T1 (VAS: 3.0 ± 1.6 vs. 4.43 ± 1.47; < 0.005) and T2 (VAS: < 0.030) compared to group A. Functional outcomes (PRTEE) also favored group B at T1 ( < 0.030) and in the pain section at T2 ( < 0.020). Grip strength improved similarly in both groups. CET thickness showed no significant differences at T3. Vascularization decreased significantly in both groups, with a non-significant trend favoring group B. The combined F-ESWT+R-PW therapy proved more effective than F-ESWT alone in the short- to mid-term management of chronic lateral epicondylitis, significantly enhancing pain reduction and functional outcomes. The combination of focal and radial pressure waves offers a superior therapeutic approach, leveraging the distinct mechanisms of each modality for better clinical results. Further research is needed to confirm these findings and establish long-term efficacy.