'Luckiest' definitions:

Definition of 'Luckiest'

From: GCIDE

Lucky \Luck"y\, a. [Compar. Luckier; superl. Luckiest.]
1. Favored by luck; fortunate; meeting with good success or good fortune; -- said of persons; as, a lucky adventurer. " Lucky wight." --Spenser. [1913 Webster]
2. Producing, or resulting in, good by chance, or unexpectedly; favorable; auspicious; fortunate; as, a lucky mistake; a lucky cast; a lucky hour. [1913 Webster]
We doubt not of a fair and lucky war. --Shak.
Syn: Successful; fortunate; prosperous; auspicious. [1913 Webster]