I can think of handful of examples of this.  In most of these cases, the 
meaning has changed to the opposite, and it's quite confusing.

"Gunning for you."  I my mind, it was just a few years ago when this meant, 
"I'm rooting for you." or "I'm behind you 100%."  Now, it's just the 
opposite.  "I'm coming after you." or "I'm going to try to stop you."  I 
believe the phrase probably originated in the trenches, and when you left 
the trench, you surely hoped that your friends were gunning for you.  Or 
perhaps it had to do with tail-gunners.  If no one was gunning for you, you 
were simply up there flying around while someone else was shooting at you! 
I can still find a couple examples of the older definition on the Web, so 
you don't think I'm just smoking crack. ;-)
http://www.definition-of.com/gunning+for+you
http://www.allwords.com/word-gun.html

"Sleeper" when referring to movies.  Someone might say, "Hey, have you seen 
the new movie yet?  I didn't expect it to be very good, but haven't heard 
very much about it."  To which one might reply, "Yeah.  It was a real 
sleeper, though!  I haven't seen a movie that good in a long time!"  Or, the 
reply might go something like this: "Yeah, but don't bother going to see it. 
It was a real sleeper."  The original definition was similar to a "sleeper" 
in the spy sense of the word.  You were surprised that the movie because it 
was far better than you expected.  Apparently, it's more common to see the 
term "sleeper hit" when used in that sense now. 
http://en.wikipedia.org/wiki/Sleeper_hit  Oddly, I can no longer find any 
examples of the "newer" usage on the Web, but then I'm probably not looking 
hard enough. I remember this question coming up last year when CNN had an 
article in which they referred to a few of the year's worst movies as 
sleepers, and it was definitely not in a good sense. When I asked my 
co-workers last year, they unanimously said that a "sleeper" was a long, 
boring movie, and I could find little information on the Web to support my 
claim that it was the opposite.  Perhaps the original meaning is gaining 
ground again.

"Showstopper" is one to keep an eye on.  In the original theatrical sense, 
it was the point that the show had to stop, because of the thunderous 
applause after a performance.  It was something really good.  When used in 
reference to software, it generally means the opposite.  You're giving a 
demonstration of the new program, and it crashes.  That's a showstopper.  I 
would expect this newer defintion to eventually make its way into common 
usage, if it hasn't already.

"Back on track" versus "untracked".  I include this one, simply because the 
two phrases apparently mean the exact same thing, but imply the opposite.  A 
few years ago, in sports columns, I kept seeing the term "untracked" used in 
a way that made no sense to me.  An example of this would be, "Tiger woods 
needs to get untracked, or he's not going to make the cut."  You could use 
the phrase "back on track" instead of "untracked" without changing the 
meaning of the sentence, even though the analogy is the complete opposite. 
"Back on track" always made me think of getting a train back on the tracks. 
"Untracked" apparently refers to getting bogged down in a deep rut, where 
the only way you're going to get out is to get your vehicle out of the deep 
tracks.

I bet if I was really old, I could come up with a lot more examples.  :-)

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