Background: Cheilectomy is a joint-sparing surgery for the treatment of moderate stages of Hallux Rigidus (HR). The purpose of this systematic review was to assess the clinical outcomes, range of motion (ROM), complications, and revision rates associated with cheilectomy. Methods: A literature search of the PubMed, Scopus, and Cochrane databases was performed. PRISMA guidelines were used. Risk of bias was assessed through the Newcastle–Ottawa Scale. Meta-analysis of the clinical outcomes scores was performed. Results: The initial search identified 317 articles, with 16 included. Cheilectomy improved ROM by 51.15% (41.23° to 62.32°), with greater gains in traditional (67.72%) vs. minimally invasive (48.74%) techniques. VAS decreased by 72.61%, more in traditional (79.35%) than minimally invasive (64.97%). AOFAS improved by 33.99%, from 61.83 to 82.85. Complications occurred in 11% (11.68% traditional, 9.73% minimally invasive), with residual pain (7.46%) more common in traditional and nerve injury (3.78%) in minimally invasive procedures. Revision rates were 7.4% overall (6.1% traditional, 8.8% minimally invasive). Conclusions: This procedure showed satisfactory results regardless of whether the traditional or minimally invasive technique is used. Current evidence does not allow for a definitive indication, but careful patient selection is advisable, particularly for mild to moderate cases.