The English language includes an interesting category of words and phrases called contronyms (also spelled  contranyms , or referred to a...

75 Contronyms (Words with Contradictory Meanings)

The English language includes an interesting category of words and phrases called contronyms (also spelled contranyms, or referred to as autoantonyms) — terms that, depending on context, can have opposite or contradictory meanings. When you use these words, be sure the context clearly identifies which meaning is intended:
1. Apology: A statement of contrition for an action, or a defense of one
2. Aught: All, or nothing
3. Bill: A payment, or an invoice for payment
4. Bolt: To secure, or to flee
5. Bound: Heading to a destination, or restrained from movement
6. Buckle: To connect, or to break or collapse
7. Cleave: To adhere, or to separate
8. Clip: To fasten, or detach
9. Consult: To offer advice, or to obtain it
10. Continue: To keep doing an action, or to suspend an action
11. Custom: A common practice, or a special treatment
12. Dike: A wall to prevent flooding, or a ditch
13. Discursive: Moving in an orderly fashion among topics, or proceeding aimlessly in a discussion
14. Dollop: A large amount (British English), or a small amount
15. Dust: To add fine particles, or to remove them
16. Enjoin: To impose, or to prohibit
17. Fast: Quick, or stuck or made stable
18. Fine: Excellent, or acceptable or good enough
19. Finished: Completed, or ended or destroyed
20. First degree: Most severe in the case of a murder charge, or least severe in reference to a burn
21. Fix: To repair, or to castrate
22. Flog: To promote persistently, or to criticize or beat
23. Garnish: To furnish, as with food preparation, or to take away, as with wages
24. Give out: To provide, or to stop because of a lack of supply
25. Go: To proceed or succeed, or to weaken or fail
26. Grade: A degree of slope, or a horizontal line or position
27. Handicap: An advantage provided to ensure equality, or a disadvantage that prevents equal achievement
28. Help: To assist, or to prevent or (in negative constructions) restrain
29. Hold up: To support, or to impede
30. Lease: To offer property for rent, or to hold such property
31. Left: Remained, or departed
32. Let: Allowed, or hindered
33. Liege: A feudal lord, or a vassal
34. Literally: Actually, or virtually
35. Mean: Average or stingy, or excellent
36. Model: An exemplar, or a copy
37. Off: Deactivated, or activated, as an alarm
38. Out: Visible, as with stars showing in the sky, or invisible, in reference to lights
39. Out of: Outside, or inside, as in working out of a specific office
40. Overlook: To supervise, or to neglect
41. Oversight: Monitoring, or failing to oversee
42. Peer: A person of the nobility, or an equal
43. Presently: Now, or soon
44. Put out: Extinguish, or generate
45. Puzzle: A problem, or to solve one
46. Quantum: Significantly large, or a minuscule part
47. Quiddity: Essence, or a trifling point of contention
48. Quite: Rather (as a qualifying modifier), or completely
49. Ravel: To entangle, or to disentangle
50. Refrain: To desist from doing something, or to repeat
51. Rent: To purchase use of something, or to sell use
52. Rock: An immobile mass of stone or figuratively similar phenomenon, or a shaking or unsettling movement or action
53. Sanction: To approve, or to boycott
54. Sanguine: Confidently cheerful, or bloodthirsty
55. Scan: To peruse, or to glance
56. Screen: To present, or to conceal
57. Seed: To sow seeds, or to shed or remove them
58. Shop: To patronize a business in order to purchase something, or to sell something
59. Skin: To cover, or to remove
60. Skinned: Covered with skin, or with the skin removed
61. Splice: To join, or to separate
62. Stakeholder: One who has a stake in an enterprise, or a bystander who holds the stake for those placing a bet
63. Strike: To hit, or to miss in an attempt to hit
64. Table: To propose (in British English), or to set aside
65. Temper: To soften, or to strengthen
66. Throw out: To dispose of, or to present for consideration
67. Transparent: Invisible, or obvious
68. Trim: To decorate, or to remove excess from
69. Trip: A journey, or a stumble
70. Unbending: Rigid, or relaxing
71. Variety: A particular type, or many types
72. Wear: To endure, or to deteriorate
73. Weather: To withstand, or to wear away
74. Wind up: To end, or to start up
75. With: Alongside, or against