This is a collection of words called "Janus-faced" or "contronyms" where the same word has contrary meanings.
WITH: a) alongside b) against
a) England fought with France against Germany.
b) England fought with France.
CLIP: a) fasten b) separate
a) Clip the coupon to the newspaper
b) Clip the coupon from the newspaper
FAST: a) firmly in one place b) rapidly from on place to another
a) The pegs held the test fast.
b) She ran fast.
BOLT: a) to secure in place b) to dart away
a) I'll bolt the door.
b) Did you see the horse bolt?
TRIM: a) add things to b) cut away
a) Let's trim the Christmas tree.
b) Let's trim the hedge.
DUST: a) remove material from b) spread material on
a) Three times a week they dust the floor.
b) Three times each season they dust the crops.
WEATHER: a) withstand b) wear away
a) Strong ships weather storms.
b) Wind can weather rocks.
HANDICAP: a) advantage b) disadvantage
a) What's your handicap in golf?
b) His lack of education is a handicap.
COMMENCEMENT: a) beginning b) conclusion
a) Beautiful weather marked the commencement of spring.
b) She won an award at her high school commencement.
HOLD UP: a) support b) hinder
a) Please hold up the sagging branch.
b) Accidents hold up the flow of traffic.
KEEP UP: a) continue to fall b) continue to stay up
a) The farmers hope that the rain will keep up.
b) Damocles hoped that the sword above his head would keep up.
LEFT: a) departed from b) remaining
a) Ten people left the room
b) Five people were left in the room.
DRESS: a) put items on b) remove items from
a) Let's dress for the ball
b) Let's dress the chicken for cooking
TEMPER: a) soften b) strengthen
a) You must temper your anger with reason.
b) Factories temper steel with additives.
CLEAVE: a) separate b) adhere firmly
a) A strong blow will cleave a plank in two.
b) Bits of metal cleave to a magnet.
STRIKE: a) secure in place b) remove
a) Use a firm grip to strike the nail.
b) When the show is over, we'll strike the set.
GIVE OUT: a) produce b) stop producing
a) A good furnace will give out enough energy to heat the house.
b) A broken furnace will often give out.
SANCTION: a) give approval of b) censure
a) The NCAA plans to sanction the event
b) Should our country impose a new sanction on Libya?
SCREEN: a) view b) hide from view
a) Tonight the critics will screen the film.
b) Defense men mustn't screen the puck.
OVERSIGHT: a) careful supervision b) neglect
a) The foreman was responsible for the oversight of the project.
b) The foreman's oversight ruined the success of the project.
QUALIFIED: a) competent b) limited
a) The candidate for the job was fully qualified.
b) The dance was a qualified success.
MOOT: a) debatable b) not worthy of debate
a) Capital punishment is a moot point.
b) That the earth revolves around the sun is a moot point.
CERTAIN: a) definite b) difficult to specify
a) I am certain about what I want in life.
b) I have a certain feeling about the plan.
MORTAL: a) deadly b) subject to death
a) The knight delivered a mortal blow.
b) All humans are mortal.
BUCKLE: a) fasten together b) fall apart
a) Safe drivers buckle their sear belts.
b) Unsafe buildings buckle at the slightest tremor of the earth.
TRIP: a) to stumble b) to move gracefully
a) Don't trip on the curb.
b) Let's trip the light fantastic.
PUT OUT: a) generate b) extinguish
a) The candle put out enough light for us to see.
b) Before I went to bed, I put out the candle.
UNBENDING: a) rigid b) relaxing
a) On the job Smith is completely unbending.
b) Relaxing on the beach is a good way of unbending.
WEAR: a) endure through use b) decay through use
a) This suit will wear like iron.
b) Water can cause mountains to wear.
SCAN: a) examine carefully b) glance at hastily
a) I scan the poem.
b) Each day, I scan the want ads.
FIX: a) restore b) remove part of
a) It's time to fix the fence.
b) It's time to fix the bull.
SEEDED: a) with seeds b) without seeds
a) The rain nourished the seeded field.
b) Would you like some seeded raisins?
CRITICAL: a) opposed b) essential to
a) Joanne is critical of our effort
b) Joanne is critical to our effort.
THINK BETTER: a) admire more b) be suspicious of
a) I think better of the first proposal than the second.
b) If I were you, I'd think better of that proposal.
TAKE: a) obtain b) offer
a) Professional photographers take good pictures.
b) Professional models take good pictures.
IMPREGNABLE: a) invulnerable to penetration b) able to be impregnated
a) The castle was so strongly built that it was impregnable.
b) Treatments exist for making a childless woman more impregnable.
BELOW PAR: a) excellent b) poor
a) Her below par score won the golf tournament.
b) I'm disappointed in you below par performance on the spelling test.
DOWN HILL: a) adverse b) easy
a) When the source of the capital dried up, the fortunes of the corporation went down hill.
b) After you switch to diet drinks, it will be all down hill for your weight-loss program.
WIND UP: a) start b) end
a) I have to wind up my watch.
b) Now I have to wind up this discussion of curious and contrary contronyms.
- Stan Niles
Source: Crazy English by Richard Lederer.