Background: Patients with a re-recurrent hernia may account for up to 20% of all incisional hernia (IH) patients. IH repair in this population may be complex due to an altered anatomical and biological situation as a result of previous procedures and outcomes of IH repair in this population have not been thoroughly assessed. This study aims to assess outcomes of IH repair by dedicated hernia surgeons in patients who have already had two or more re-recurrences. Methods: A propensity score matched analysis was performed using a registry-based, prospective cohort. Patients who underwent IH repair after ≥ 2 re-recurrences operated between 2011 and 2018 and who fulfilled 1 year follow-up visit were included. Patients with similar follow-up who underwent primary IH repair were propensity score matched (1:3) and served as control group. Patient baseline characteristics, surgical and functional outcomes were analyzed and compared between both groups. Results: Seventy-three patients operated on after ≥ 2 IH re-recurrences were matched to 219 patients undergoing primary IH repair. After propensity score matching, no significant differences in patient baseline characteristics were present between groups. The incidence of re-recurrence was similar between groups (≥ 2 re-recurrences: 25% versus control 24%, p = 0.811). The incidence of complications, as well as long-term pain, was similar between both groups. Conclusion: IH repair in patients who have experienced multiple re-recurrences results in outcomes comparable to patients operated for a primary IH with a similar risk profile. Further surgery in patients who have already experienced multiple hernia re-recurrences is justifiable when performed by a dedicated hernia surgeon.