Introduction: Digitalization offers significant potential benefits to ultrasound education. This study compares the effectiveness of webinar teaching against face-to-face teaching in providing theoretical competencies in certified head and neck ultrasound (HNUS) courses. Patients and methods: This prospective, controlled, multicenter study was conducted in 2023 at three universities with certified HNUS courses. One course used webinar lessons (S), and the others used face-to-face teaching (C). The control group courses (C) were held on two consecutive days. The first day of the study group course was held as a webinar (S) 1 week before the second day and was also recorded for preparatory purposes. All participants completed three assessments: a pre-course self-evaluation (Evaluation^pre), a post-course self-evaluation (Evaluation^post), and a post-course theory test (Theory Test^post). The evaluations used a Likert scale (1–7) to record the participants’ subjective assessments of competencies and attitudes toward webinar teaching. Theory Test^post included multiple-choice and free-answer questions on the sonographic pathologies of lymph nodes, the soft tissue of the neck, and salivary glands. A group of inexperienced medical students (V) completed the Theory Test^post for validation purposes. Result: 128 data sets were analyzed (31 S; 30 C; 47 V). Both groups, S and C, rated their competencies after the courses significantly higher than before (p < 0.01) but at a similar level in comparison with each other (p = 0.34). Both groups supported teaching theoretical content through webinars (S: 6.7 ± 0.5 vs. C: 6.2 ± 0.9). Both groups achieved similar results in the Theory Test^post (p = 0.54), significantly outperforming the validation group (p < 0.001). Conclusion: Our data suggest that webinars can be an effective alternative to face-to-face lessons in teaching theoretical competencies in HNUS. Participants gave overall positive evaluations of digital teaching methods. Our findings support evidence that digital learning methods are valuable for modern ultrasound education.