In current practice, single-shot spinal anesthesia has traditionally been performed using the conventional surface-anatomic-Landmark-Guided technique. This “blind” technique has significant critical issues such as a high risk of complications due to the numerous attempts at spinal needle placement and the negative impact on the learning curve of the trainees. Ultrasound-Assisted spinal anesthesia could reduce these critical issues and allow trainees to perform the procedure more easily and with fewer complications for the patient. We performed a before-and-after monocentric retrospective comparative study at the University of Naples “Federico II” (Naples, Italy). Inclusion criteria were as follows: patients aged 18 years or older; ASA physical status between I and IV; and elective orthopedic surgery under single-shot spinal anesthesia performed by supervised trainees between January 2022 and December 2022. In the selected cohort, 88 patients were included in group A (Landmark-Guided spinal anesthesia) and 91 in group B (Ultrasound-Assisted spinal anesthesia). The number of attempts by trainees (p-value < 0.005), procedure performing time (<0.001), and patient discomfort (<0.001) were significantly lower in group B than in group A. Ultrasound-Assisted single-shot spinal anesthesia performed by novice trainees reduces the number of attempts, complication rate, periprocedural pain, and patient discomfort.