Background: Dermoscopy of morphea and cutaneous lichen sclerosus (CLS) has been described by various studies, with none of them considering variability according to clinical phases and investigating dermoscopic-histological correlations. Objective: To evaluate dermoscopic features in general and according to clinical stage, identify possible distinctive dermoscopic clues, and assess dermoscopy accuracy in detecting subclinical alterations in morphea and CLS. Methods: A representative dermoscopic image of target lesions was evaluated for the presence of specific features, correlating them with clinical subtype (inflammatory, inflammatory-sclerotic, sclerotic, or sclerotic-atrophic). In case of clinical-dermoscopic discordance (inflammatory, sclerotic, and atrophic findings in noninflammatory, nonsclerotic, and nonatrophic lesions, respectively), dermoscopic-pathological correspondence was assessed. Results: A total of 86 lesions (51 morphea/35 CLS) were analyzed, with most of them displaying an inflammatory-sclerotic or sclerotic clinical pattern. The most common dermoscopic findings of morphea were “fibrotic beams,” while CLS was mainly characterized by bright white/white-yellowish patches and yellowish-white keratotic follicular plugs; all these structures displayed complete specificity for the correspondent dermatosis. Additionally, pigmentary structures were significantly more frequent in morphea and white scaling and hemorrhagic spots in CLS. Only few dermoscopic features reached a statistical significance for a specific clinical stage. Regarding the clinical-dermoscopic discordance rate, it was significantly more common in morphea than CLS; in all cases there was a correspondence between dermoscopic and pathological findings. Conclusion: Dermoscopy of morphea and CLS reveals distinctive dermoscopic clues which are often unrelated to clinical stage but show a constant histological correspondence, thus emphasizing its usefulness in diagnosis and therapeutic management of these conditions.