Background: Pathologic complete response (pCR, pT0N0M0) or pathologic downstaging (pDS, <pT2N0M0) for bladder cancer is associated with increased overall survival (OS). However, some patients who achieved pCR or pDS experience recurrence, but these patients have not been targeted for adjuvant immunotherapy in studies to date, and the prognosis has not been well studied. We aim to examine the prognosis for bladder cancer patients with recurrence after pCR or pDS after radical cystectomy (RC). Methods: Of the 1562 patients who underwent a RC for bladder cancer between June 1996 and November 2023, 712 (45.6%), including 29 patients who did not undergo lymph node dissection, were identified as having pCR or pDS on final pathology. Of the 712 patients, 108 (15.2%) experienced recurrence. Results: Among 712 patients, 170 (23.9%) achieved pCR, 305 (42.8%) in pT1, 140 (19.7%) in Tis, and 97 (13.6%) in Ta. Out of the 170 patients with pCR, 12 (7.1%) experienced recurrence. Among the 305 patients with pT1, recurrence occurred in 63 (20.7%), and out of the 140 patients with Tis and 97 with Ta, 24 (17.1%) and 9 (9.3%) had recurrence, respectively. Only 150 (21.1%) patients received neoadjuvant chemotherapy (NAC), and 30 (27.8%) of the 108 patients who relapsed had received NAC. The median age of 108 patients with recurrence was 66.8 years old (range 31.3–86.2), and variant histology was observed in 10 (9.3%) surgical specimens. At a median follow-up of 36.7 months, the median time to recurrence was 15.5 months (10.4–20.6). Sixty-seven patients (62%) had local recurrence or lymph node-only metastasis. The distant metastasis was most common in the lung, liver, and bone (42, 38%). Conclusions: Patients with pCR or pDS at the time of radical cystectomy should prudently undergo surveillance, as recurrence and metastasis can still develop. Future studies are needed to reinforce these findings and decide whether to receive adjuvant treatment in the post-NAC setting.