Recently, the Low Window technique was proposed to facilitate sinus augmentation and reduce postsurgical patient discomfort. It was shown to be both safe and effective. This case series evaluates the postsurgical discomfort of patients undergoing Low Window sinus augmentation, the bone gain achieved, and whether these factors correlate with the osteotomy area. Records of patients (n = 26) who underwent a sinus elevation using the Low Window approach (n = 34 interventions), followed by implant placement and prosthetic rehabilitation (n = 97 implants), were assessed retrospectively. The analyzed outcomes were the medial, middle, and lateral bone gain ≥ 9 months after augmentation; pain at 5 to 6 hours postsurgery, evaluated on a visual analog scale (VAS; 0 to 100); pain, swelling, and hematoma formation every day up to 7 days postsurgery, evaluated by VAS; implant and prosthetic success and survival rates; and rate of complications. The average follow-up time was 62.1 ± 14.9 months. No intraoperative sinus membrane perforations or other complications occurred. Medial, middle, and lateral bone gains were 10.1 ± 1.7 mm, 11.6 ± 0.8 mm, and 10.7 ± 0.9 mm, respectively. At the last follow-up, the implant success rate was 99%. Postsurgical VAS pain 5 to 6 hours postsurgery was 12.3 ± 8.0 and decreased significantly thereafter. Swelling prevalence was 29.4% at 1 day postsurgery, 20.6% at 2 days, and 2.9% the following day. No swelling was observed from day 4 onward. Prevalence of hematoma was 8.8% for 2 days postsurgery, 2.9% the day after, and no hematoma was observed thereafter. Only the osteotomy area correlated with immediate postsurgical pain, but not with other discomfort outcomes or with bone gain. Low Window sinus elevation might allow bone gain and medium-term implant and prosthetic success rates similar to that of other access window designs. Prospective, comparative studies are needed to investigate whether the technique is more advantageous than traditional approaches.