Background: Migraine impairs daily functioning, and concerns persist about underdiagnosis, inappropriate pharmacotherapy, and medication-overuse headache (MOH). Triptan access has widened in Japan, with stepped-care guidance, yet avoiding overuse remains difficult. Methods: Using NDB Open Data Releases 1–9 (FY2014–FY2022), we quantified annual outpatient and community-pharmacy triptan prescriptions. Volumes were stratified by sex, drug, and 5-year age bands, and absolute/percentage changes were calculated versus FY2014. To contextualize age-structure shifts, we referenced total patient counts for ICD-10 G43 from the e-Stat Patient Survey (2014, 2017, 2020, 2023). Associations between sex and drug were tested by chi-square on contingency tables aggregated across releases. Results: Total prescriptions approximately doubled by FY2022 (31,095,293 tablets), comprising 6,219,190 for males and 24,876,103 for females (~4-fold female predominance). All five triptans increased, with the largest gains for rizatriptan (~2.3×) and eletriptan (~2.2×). The greatest increases occurred in males aged 15–19 years (~2.78×) and 60–64 years (~2.73×) and in females aged 55–59 years (~2.58×) and 15–19 years (~2.56×). The modal age band shifted from 40–44 years in FY2014 to 45–49 years in FY2022. Sex-by-drug distribution differed significantly (χ², p<0.0001); in FY2022, rizatriptan predominated in males (followed by sumatriptan) and eletriptan in females (followed by rizatriptan). Conclusions: From 2014 to 2022, triptan use in Japan rose with persistent female predominance, growth among adolescents (particularly males) and middle-to-older adults, and an older peak age. Findings suggest contributions from expanded care-seeking, rising social burden, chronification, and MOH. Multilevel actions—early diagnosis, rational use with MOH prevention, school/workplace support, timely specialist referral, and proactive pharmacist engagement—are warranted.