The aim of this study was to identify dementia trajectories and their associated predictors among elderly Taiwanese people over a 14-year period using a nationwide representative longitudinal study. This retrospective cohort study was performed using the National Health Insurance Research Database. Group-based trajectory modeling (GBTM) was used to distinguish the specific trajectory groups of incident dementia during 2000–2013. All 42,407 patients were classified by GBTM to identify the trajectory of incident dementia, which included high- (n = 11,637, 29.0%), moderate- (n = 19,036, 44.9%), and low-incidence (n = 11,734, 26.1%) groups. Those diagnosed with hypertension (adjusted odds ratio [aOR] = 1.43; 95% confidence interval [CI] = 1.35–1.52), stroke (aOR = 1.45, 95% CI = 1.31–1.60), coronary heart disease (aOR = 1.29, 95% CI = 1.19–1.39), heart failure (aOR = 1.62, 95% CI = 1.36–1.93), and chronic obstructive pulmonary disease (aOR = 1.10, 95% CI = 1.02–1.18) at baseline revealed tendencies to be classified into high-incidence groups in dementia risk. The results from a 14-year longitudinal study identified three distinct trajectories of incident dementia among elderly Taiwanese people: patients with cardiovascular disease risk factors and cardiovascular disease events tended to be classified into high-incidence dementia groups. Early detection and management of these associated risk factors in the elderly may prevent or delay the deterioration of cognitive decline.