Individuals with chronic liver disease (CLD) have an increased risk of bleeding from thrombocytopenia and changes in hemostasis. The aim of this study was to evaluate the frequency of and the factors associated with the occurrence of bleeding in CLD patients who underwent dental surgical procedures. This was a retrospective study whose data were collected in a hospital dentistry service between 2010 and 2016. The patients were referred from the gastroenterology and liver transplantation services of a university hospital for dental treatment. The study followed the STROBE guidelines. Among the 71 surgical procedures performed, there were 17 (24%) perioperative and postoperative bleeding episodes, 14 of which were in pretransplant patients and 11 received blood transfusion before dental surgery. Individuals with a previous history of bleeding (PR = 2.67, CI = 1.07–6.67, P = 0.035) and those with a platelet count before surgery 50 × 109/l or less (PR = 7.48, CI = 1.70–32.86, P = 0.008) had a higher prevalence of perioperative and postoperative bleeding episodes than their peers without a previous history of bleeding, and those with platelet count greater than 50 × 109/l. The approach to individuals with CLD is complex and represents a challenge to the clinician. A careful anamnesis combined with laboratory screening of coagulation disorders appears to be useful to identify individuals at a major risk of bleeding. Studies identifying the predisposing factors of bleeding in CLD patients support well tolerated protocols for oral surgery in this group.