Objectives The aim of the study is to compare proportions of venous leg ulcers healed in patients treated with two different sub-bandage pressure values in relation to age. Methods The study included 102 outpatients with venous leg ulcers, one group with moderate compression pressure of 35–40 mmHg and the second with high pressure >45 mmHg. Each group was divided into two subgroups according to the age (≥65 vs. <65 years). Computerized planimetry was used to measure the size of the ulcers at 6, 12, 18 and 24 weeks. Results Kaplan–Maier analysis showed high pressure leads to higher proportion of healed venous leg ulcers, compared to moderate pressure, in patients aged ≥65 years (57.6% vs. 28%) and in patients <65 years (53.8% vs. 36%) (p < 0.05). Conclusion The study showed that higher compression pressure leads to higher proportions of venous leg ulcers healed, independent of age and could be safely preferred in older patients.