Etymology
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sleepless (adj.)

early 15c., from sleep (n.) + -less. Old English had slæpleas but the modern word seems to be a re-formation. Similar formation in German schlaflos, Dutch slapeloos. Related: Sleeplessly; sleeplessness.

updated on April 03, 2014

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Definitions of sleepless from WordNet

sleepless (adj.)
experiencing or accompanied by sleeplessness; "twenty watchful, weary, tedious nights"- Shakespeare;
lay sleepless all night
Synonyms: insomniac / watchful
sleepless (adj.)
always watchful; "to an eye like mine, a lidless watcher of the public weal"- Alfred Tennyson;
Synonyms: lidless
From wordnet.princeton.edu, not affiliated with etymonline.