skipper

1 [skip-er]
noun
1.
the master or captain of a vessel, especially of a small trading or fishing vessel.
2.
a captain or leader, as of a team.
verb (used with object)
3.
to act as skipper of.

Origin:
1350–1400; Middle English < Middle Dutch schipper, equivalent to schip ship + -er -er1

Dictionary.com Unabridged

skipper

2 [skip-er]
noun
1.
a person or thing that skips.
2.
any of various insects that hop or fly with jerky motions.
3.
any of numerous quick-flying, lepidopterous insects of the family Hesperiidae, closely related to the true butterflies.
4.
saury ( def 1 ).

Origin:
1200–50; Middle English: locust. See skip1, -er1

Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
skipper1 (ˈskɪpə)
 
n
1.  the captain of any vessel
2.  the captain of an aircraft
3.  a manager or leader, as of a sporting team
 
vb
4.  to act as skipper (of)
 
[C14: from Middle Low German, Middle Dutch schipper shipper]

skipper2 (ˈskɪpə)
 
n
1.  a person or thing that skips
2.  any small butterfly of the family Hesperiidae, having a hairy mothlike body and erratic darting flight
3.  another name for saury

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
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Etymonline
Word Origin & History

skipper
"captain or master of a ship," late 14c., from M.Du. scipper, from scip (see ship). Transfered sense of "captain of a sporting team" is from 1830.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
When a skipper dies or retires, his quota goes back into a pool to be
  re-allocated.
As the skipper landed us on the first of the rocks, the cries of the crested
  terns became deafening.
The skipper is an architect and the crew is also not what would be called rich
  in the vernacular.
With that and a prayer, the skipper was able to steer the freighter to safety.
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