Background/Objective: We assessed the analgesic and anti-inflammatory effects of kale extract (500 mg anthocyanin equivalent) in patients after mandibular molar surgery. Methods: In our randomized clinical trial, postoperative subjects (n = 20) aged 18–25 years old took kale extract or ibuprofen (400 mg) capsules for 7 days, or vice versa, after surgical removal of each impacted tooth. Their pain intensity was then assessed using a visual analogue scale (VAS). Moreover, salivary α-amylase (AA) activity, matrix metalloproteinase 9 (MMP-9) and transforming growth factor beta2 (TGF-β2) concentrations were measured. Levels of VAS and AA decreased 7 days after the first and second molar extractions in the two treatment groups. Results: The kale extract was more effective than ibuprofen. MMP-9 and TGF-β2 levels were reduced on days 4 and 7 following the two extractions in the kale group, whereas they were reduced on days 4 and 7 following the first extraction in the ibuprofen group. There was a positive correlation between MMP-9 and TGF-β2. Thus, the consumption of the kale extract exerted analgesic and anti-inflammatory effects during the postoperative period in patients who had undergone molar extractions. In conclusion, anthocyanin-abundant kale extract is preferable when administered in a postoperative course and could reduce the need for a prescription of ibuprofen.