Hypertension is a risk factor for incident heart failure (HF). However, the effect of uncontrolled blood pressure (BP) on incident HF in older adults with hypertension has not been prospectively examined in propensity-matched studies. Of the 5795 Cardiovascular Health Study participants, ≥65 years, 2562 with self-reported physician-diagnosed hypertension had no baseline HF. Of these, 1391 had uncontrolled hypertension, defined as systolic BP (SBP) ≥140 (n = 1373) or diastolic BP ≥90 mm Hg (n = 18). Propensity scores for uncontrolled hypertension, calculated for each participant, were used to assemble a cohort of 1021 pairs of participants with controlled and uncontrolled hypertension who were balanced on 31 baseline characteristics. Centrally adjudicated incident HF developed in 23% and 26% of participants with controlled and uncontrolled hypertension respectively during 13 years of follow-up (matched hazard ratio [HR] when uncontrolled hypertension was compared with controlled hypertension, 1.39; 95% confidence interval [CI], 1.12 to 1.73; P = .003). HRs (95% CI) for incident HF for those with (n = 503) and without (n = 1539) chronic kidney disease (CKD) were 1.73 (95% CI, 1.26 to 2.38; P = .001) and 1.08 (95% CI, 0.87 to 1.34; P = .486) respectively (P for interaction, .012). Compared with participants with controlled hypertension, HRs for incident HF associated with SBP 140 to 159 and ≥160 mm Hg were 1.06 (95% CI, 0.86 to 1.31; P = .572) and 1.58 (95% CI, 1.27 to 1.96; P < .0001), respectively. In community-dwelling older adults with hypertension, those with uncontrolled (versus controlled) BP have increased risk of new-onset HF, which is more pronounced in those with SBP ≥160 mm Hg and with CKD.