Extracorporeal shockwave therapy (ESWT) has been shown to reduce wound dimensions and healing time in chronic wounds and should be considered a valuable tool in the healing of chronic complex lower extremity wounds. The aim of this small case series was to evaluate the effect of ESWT on complex chronic wounds in patients with multiple comorbidities in a medically underserved outpatient wound care clinic setting. All patients had baseline wound measurements taken. Pictures of the wounds were also taken at the time of the initial visit. Patients selected for ESWT received weekly treatments for a maximum recorded duration of 12 weeks in the form of focused electro-hydraulic acoustic pulses. Wound beds were cleansed according to standard of care. Thirteen patients were followed with a total of 18 wounds treated. After retrospectively analyzing the data, 3 subjects and a total of 5 wounds were excluded, leaving 10 total subjects and 13 wounds. Out of these wounds, 12 healed completely by or before week 12 of ESWT. All wounds demonstrated significant wound dimension reduction during the first 12 weeks of treatment. ESWT could offer accessible, fast, safe, and cost-effective management of some complex chronic wounds. Further research is needed to validate these findings.