Background Fingernail onychomycosis differs clinically from toenail disease. While toenail onychomycosis has been extensively studied, research investigating demographic characteristics, histopathology, and causative organisms as prognostic factors for cure specifically in fingernail cases remains notably limited. Although prognostic factors for toenail onychomycosis have been extensively documented, these findings cannot be directly extrapolated to fingernail infections due to distinct environmental and occupational exposures. Consequently, conducting a direct comparative study between these two anatomical sites remains challenging and represents an important avenue for future research. Objectives This retrospective cohort study aims to identify prognostic factors associated with the cure of fingernail onychomycosis. Methods This study included patients aged 18 years or older diagnosed with fingernail onychomycosis who underwent histopathological examination of nail specimens, excluding those with incomplete records. Clinical evaluation and laboratory investigation were studied. Descriptive statistics, chi‐square tests, and independent t‐tests were utilized for data analysis. Results A total of 45 patients (predominantly female, 71.1%) with a mean age of 48.0 ± 20.5 years were enrolled. Distal and lateral subungual onychomycosis and proximal subungual onychomycosis were found in 38 (84.4%) and 7 (15.6%) patients, respectively. Ring finger involvement (18 cases, 40.0%) was significantly associated with younger patients (p = 0.003) and presented with periungual inflammation at the proximal nail fold (p = 0.021). Thirteen cases (28.9%) failed to respond to standard systemic therapy. Within the population with ring finger involvement, the treatment failure rate was 55.6% (10 out of 18 cases). These nonresponders were significantly younger (p = 0.014), more likely to have ring finger involvement (p = 0.001) and presented with septate hyphae on histology (100.0%, p = 0.010). Conclusion Onychomycosis of the ring finger in young patients was observed to be recalcitrant to treatment, suggesting that these cases may require closer monitoring or alternative therapeutic approaches in clinical practice. Histopathological features, including mold invasion of the nail plate and polymorphonuclear cells infiltration, tended to be found in treatment failure cases.