How to write a leading apostrophe in Word

Disclaimer: I don't work on the Office team.

Word has a smart quotes feature where it will automagically transform

straight "double quotes," 'single quotes,' and greengrocer's apostrophes

into

curly “double quotes,” ‘single quotes,’ and greengrocer’s apostrophes

as you type.  You send a Unicode Character 'APOSTROPHE' (U+0027) to Word, and Word turns it into a Unicode Character 'LEFT SINGLE QUOTATION MARK' (U+2018) or a Unicode Character 'RIGHT SINGLE QUOTATION MARK' (U+2019) as appropriate.  If you type it at the beginning of a word, it's an opening-single-quote; if you type it in the middle of a word, it's an apostrophe; if you type it at the end, it's either an apostrophe or a closing-single-quote, but both are the same character, so it doesn't matter.

Right?

Usually.

The apostrophe is occasionally used at the beginning of a word, to mark elided letters.  Word has trouble with this.

‘Twas brillig, and the slithy toves did gyre and gimbol in the wabe.

    -- Jabberwocky

I want to give the Word folks credit here.  A common use of an apostrophe at the beginning of a word is to abbreviate a year.  Word gets this right (I'm using Word 2010 with default settings:)

Check it out: a ’57 Chevy!

But Word also gets it wrong when you want to single-quote a clause that begins with a number:

“They were singing ’99 bottles of beer on the wall’.”

Also, if you pluralize the date, Word gets suckered:

’10 models on sale! Check out the new ‘11s!

Little nifties, from the ‘50s, innocent and sweet;
Sexy ladies from the ‘80s, who are indiscreet
    -- 42^nd Street

For those times when Word gets it wrong, here's how to fix it.

If you want to type a word that starts with an apostrophe:

1. Type the apostrophe.  Word assumes you want an opening quote.  Fine
   ‘
2. Type the apostrophe again.  Word shrugs its shoulders and gives you a closing quote in a little soixante-neuf of punctuation.
   ‘’
3. Type the magic sequence:
   
   1. Left arrow
   2. Backspace
   3. Right arrow
   ’
4. Et voilà.  Continue typing your word.
   ’Twas 

If you want to use an opening single quote with a sentence that starts with a number:

1. Type the opening quote and the number in its entirety.  So far, so good.
   ‘99
2. Type the word breaker (usually a space.)  Word "helpfully" turns the opening single quote into an apostrophe.
   ’99 
3. Invoke "Undo" via your favorite mechanism (I prefer Ctrl-Z since I'm already on the keyboard.)
   ‘99 
4. Et voilà.  Continue typing your quoted clause.
   ‘99 bottles of beer on the wall

That "Undo" tip is actually a fairly powerful curative against all sorts of Word voodoo.