Background: The axilla is a region of fundamental importance for the implications during oncological surgery, and there are many classifications of axillary lymph node subdivision: on the basis of studies on women with breast cancer, we used Clough’s and Li’s classification. However, currently we do not have a gold-standard classification regarding axillary lymphatic drainage in melanoma patients. Purpose: Our aim was to evaluate how these classifications could be adapted to sentinel lymph node evaluation in skin-melanoma patients and to look for a possible correlation between the most recent classifications of axillary lymph node location and Oeslner’s classification, one of the most common anatomical classifications still widespread today. Methods: We analyzed data from 21 patients who underwent sentinel lymph node biopsy between January 2021 and January 2022. Results: Our study demonstrates that, to an extent, there is a possible difference in the use of the various classifications, hinting at possible limits of each. The data we obtained underline how cutaneous melanoma presents extremely heterogenous lymphatic drainage at the level of the axillary cavity. However, the limited data in our possession do not allow us to obtain, at the moment, results that are statistically significant, although we are continuing to enroll patients and collect data. Conclusions: Results of this study support the evidence that the common classifications used for breast cancer do not seem to be exhaustive. Therefore, a specific axillary lymph node classification is necessary in skin melanoma patients.