Introduction: Chronic postoperative inguinal pain (CPIP) is the most common complication after inguinal hernia operation. Eighteen percent (range, 0.7%–75%) of patients suffered from CPIP after open inguinal hernia repair and 6% (range, 1%–16%) reported CPIP after laparoendoscopic groin hernia repair. The incidence of clinically significant CPIP with impact on daily activities ranged between 10% and 12%. Debilitating CPIP with severe impact on normal daily activities or work was reported in 0.5%–6% of the cases. Materials and methods: PubMed, Medline, Embase, and the Cochrane Database were searched for studies on risk factors for chronic pain after open and endoscopic hernia repair. A systematic review of the literature was conducted using the grading of recommendations, assessment, development, and evaluations (GRADE) methodology. Results: Risk factors for CPIP with strong evidence include female gender, young age, high intensity of preoperative pain, high early postoperative pain intensity, history of chronic pain other than CPIP, operation for a recurrent hernia, and open repair technique. Risk factors for CPIP with moderate evidence include postoperative complications, neurolysis, and preservation of the ilioinguinal nerve in Lichtenstein repair. Risk factors for CPIP with low evidence include genetic predisposition (DQB1*03:02 HLA haplotype), lower preoperative optimism, high pain intensity to tonic heat stimulation, inadequate suture/staple/clip mesh fixation, ignorance of the inguinal nerves, less experienced surgeon, sensory dysfunction in the groin, and worker’s compensation. Conclusion: Detailed knowledge of the risk factors, meticulous operative technique with profound knowledge of the anatomy, proper nerve identification and handling, optimization of prosthetic materials, and careful fixation are of utmost importance for the prevention of CPIP.