Background and Objectives: In this study, we aimed to evaluate pain intensity in patients after pilonidal disease surgeries of varying extent using pressure algometry and the visual analog scale and to explore potential correlations between these methods. Materials and Methods: A total of 78 adult patients with symptomatic pilonidal cysts were enrolled in this study. The patients were divided into two groups based on the type of surgery assigned to each patient at the pre-hospital consultation: pit-picking surgery (n = 39) and radical excision (n = 39). The pain levels at the surgical site were assessed and compared using the visual analog scale (VAS) and pressure algometry the morning before surgery and the day after the operation. Results: There was no statistically significant difference (p > 0.05) in VAS measurement results between surgical groups when comparing pain intensity experienced by patients before, during, and after surgery. Notably, specific pressure algometry variables (pressure pain tolerance left 2.05 ± 1.46 compared to 1.42 ± 0.73 kg/cm2, p = 0.02; maximum pressure pain tolerance left 2.91 ± 1.33 compared to 2.32 ± 1.14 kg/cm2, p = 0.04; maximum pressure pain tolerance center 2.51 ± 1.07 compared to 1.91 ± 0.91 kg/cm2, p = 0.01; interval of pressure pain tolerance center 0.98 ± 0.62 compared to 0.59 ± 0.39 kg/cm2, p = 0.00) on the first postoperative day were significantly lower in the "pit-picking" group compared to the excision group. Furthermore, no statistically significant correlation was found between VAS and pressure algometry measurements either before surgery or on the first postoperative day. Conclusions: In the early postoperative period following pilonidal disease surgery of varying extents, pain measured with the VAS does not differ. In contrast, the pressure algometry method showed greater pain in the minimally invasive surgery cohort on the first postoperative day. However, further larger studies are needed to compare these pain assessment methods in reporting pain intensity experienced during patient movement.