Background: The insertion of local anesthetic solution remains one of the most dreaded events during dental treatment, and discomfort from needle penetration is a recognised source of dental anxiety and treatment avoidance. Topical anesthetic gels and pre-injection cooling (cryotherapy) have both been proposed to reduce this discomfort, yet direct comparisons in adult endodontic patients are limited. Objective: To compare pain perception during administration of local anesthesia following a 2% lignocaine topical gel versus a standardized ice-stick cryotherapy protocol. Materials and Methods: In this two-arm crossover randomized controlled trial, patients aged 18–60 years requiring endodontic treatment in at least two teeth received both protocols at separate sites: 2% lignocaine gel (Group A) for 1 minute and a customized ice stick measuring 5 mm × 10 mm (Group B) for 15 seconds before injection. Injection pain was self-rated on a 10 cm visual analogue scale (VAS), and scores were compared using the Mann–Whitney U test at a 5% level of significance. Results: The mean VAS score was 3.65 ± 1.00 in Group A and 2.53 ± 0.94 in Group B, a statistically significant difference (z = −2.888, p = 0.004) indicating lower injection pain with cryotherapy. Conclusion: Pre-injection cryotherapy using a standardized ice stick produced significantly less injection pain than 2% lignocaine topical gel. It offers a simple, inexpensive and non-pharmacological chairside adjunct that can be readily incorporated into routine endodontic practice.