OUTSAIL Meaning of OUTSAIL in English (ˈ) ̷ ̷| ̷ ̷ transitive verbEtymology: out- + sail : to surpass in sailing : sail faster than : outstrip outsailed the earlier Roman ships — G.S.L.Clowes Webster's New International English Dictionary. Новый международный словарь английского языка Webster. 2012