Purpose <p>Most existing minimally invasive lateral ankle ligament reconstructions rely on freehand drilling techniques. The aim of this study was to assess the accuracy of bone tunnel entrances and clinical outcomes following arthroscopic anatomic lateral ligaments reconstruction using a novel drill-guiding system.</p> Methods <p>From 2020 to 2022, twenty-seven chronic lateral ankle instability cases were treated with arthroscopic ankle lateral ligaments reconstruction using a novel drill-guiding system. The accuracy of the bone tunnel entrances was assessed on postoperative computer tomographic (CT) scans. The Foot and Ankle Ability Measurement (including activities of daily living and sports subscales) and Cumberland Ankle Instability Tool (CAIT) were evaluated at the preoperative and final follow-ups. The complications were also recorded.</p> Results <p>The average follow-up time was 29.3 ± 9.0 months (range: 24–48); the final FAAM-ADL, FAAM-SS, and CAIT scores were improved significantly, compared with preoperative scores (47.4 ± 4.4 vs. 77.6 ± 3.6, 13.0 ± 2.1 vs. 28.5 ± 1.3, 21.6 ± 4.6 vs. 90.0 ± 5.1, respectively, <i>P</i> &lt; 0.001). No severe deviation (&gt;2&#xa0;mm) of bone tunnel entrances was observed. The fibular and talar bone tunnel entrances showed higher accuracy without deviation (85.2% and 88.9%, respectively), compared with calcaneal bone tunnel entrances (66.7%). There is no obvious influence between the deviation of the bone tunnel entrances and clinical outcomes. No infection, nerve injuries, and recurrence of ankle instability was encountered. One patient required removal of the fibular button due to local irritation.</p> Conclusions <p>This arthroscopic anatomic lateral ankle ligament reconstruction technique, utilizing a novel drill-guiding system, demonstrated accurate bone tunnel entrance placement and achieved favorable clinical outcomes.</p> Level of evidence <p>Level IV, Retrospective case series.</p>