The association between pre‐transplant dialysis duration and post‐transplant outcomes may vary by the population and endpoints studied. We conducted a population‐based cohort study using linked healthcare databases from Ontario, Canada including kidney transplant recipients (n = 4461) from 2004 to 2014. Our primary outcome was total graft failure (i.e., death, return to dialysis, or pre‐emptive re‐transplant). Secondary outcomes included death‐censored graft failure, death with graft function, mortality, hospitalization for cardiovascular events, hospitalization for infection, and hospital readmission. We presented results by pre‐transplant dialysis duration (pre‐emptive transplant, and .01–1.43, 1.44–2.64, 2.65–4.25, 4.26–6.45, and 6.46–36.5 years, for quintiles 1–5). After adjusting for clinical characteristics, pre‐emptive transplantation was associated with a lower rate of total graft failure (adjusted hazard ratio [aHR] .68, 95% CI: .46, .99), while quintile 4 was associated with a higher rate (aHR 1.31, 95% CI: 1.01, 1.71), when compared to quintile 1. There was no significant relationship between dialysis duration and death‐censored graft failure, cardiovascular events, or hospital readmission. For death with graft function and mortality, quintiles 3–5 had a significantly higher aHR compared to quintile 1, while for infection, quintiles 2–5 had a higher aHR. Longer time on dialysis was associated with an increased rate of several adverse post‐transplant outcomes.