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The relationship between fungal species and their resistance patterns in vineyard soils has important implications for agriculture and medicine. This study explored the prevalence of <i>Aspergillus</i> section <i>Fumigati</i> species and their resistance to azole compounds in Romanian vineyard soils. Methods: A total of 265 soil samples from various Romanian vineyards were screened for fungi resistant to azoles. Results: <i>Aspergillus</i> section <i>Fumigati</i> isolates exhibited significant resistance to itraconazole and voriconazole, but no azole-resistant <i>Aspergillus fumigatus</i> strains were detected. Six percent of the samples were positive for <i>Aspergillus</i> section <i>Fumigati</i> strains, all of which were azole-resistant. The strains were mainly <i>Aspergillus udagawae</i> (93.75%) and <i>Aspergillus lentulus</i> (6.25%). The predominant azole-resistant <i>Aspergillus</i> species were <i>Aspergillus</i> section <i>Nigri</i> strains, which were found in 75 soil samples. Conclusions: This study highlights the importance of understanding fungal resistance in vineyard soils for both the agricultural and clinical sectors. The presence of resistant strains may affect vine health and wine production while also constituting a challenge in the selection of effective treatments against severe and potentially fatal fungal infections in humans, stressing the importance of species-specific antifungal resistance knowledge.