Background: Patients with chronic rhinosinusitis with nasal polyps (CRSwNP) and asthma have poorer outcomes after functional endoscopic sinus surgery (FESS) and higher recurrence rate. The aim of present study was to investigate the long-term clinical outcomes of extended surgical strategies for patients with recurrent CRSwNP and asthma. Methods: Eighty-one patients with CRSwNP and asthma were enrolled in this 5-year prospective study. They were randomly assigned to undergo FESS, radical endoscopic sinus surgery (RESS), or RESS+Draf 3 surgery. Disease severity and clinical outcomes were evaluated using symptoms scoring, endoscopic scoring system, computed tomography staging system, sinus-specific quality of life scores, tissue and peripheral blood eosinophil percentage, and pulmonary function tests. Baseline, 1-year, 3-year, and 5-year follow-up data were compared among the groups. Results: RESS and RESS+Draf 3 strategies yielded better short-term (1 year) outcomes than did FESS. FESS had a higher short-term recurrence rate, although recurrence rates were similarly high (95.6-96.1%) in all the groups at 5 years postoperatively. RESS and RESS+Draf 3 yielded a lower long-term revision surgery rate and a longer time to recurrence post-surgery than FESS, which was negatively correlated with tissue and peripheral blood eosinophil percentage. Conclusions: CRSwNP with asthma is a systemic disease that inevitably recurs. Radical surgery prolongs recurrence time and improves olfaction, rhinorrhea, and quality of life in the short-term. Combining Draf 3 with RESS did not yield better clinical outcomes than RESS alone; thus, although RESS alone appears to be the best option, these findings need to be confirmed in further studies involving more patients, longer follow-up duration and stricter standardized medication use especially the adequate steroid irrigations.