I've been discussing with a colleague which apostrophe/single quote to actually use in what situations.

  • We've agreed to use the closing single quote ( ’ ) for possession. e.g. That’s his potato.
  • Or in a quote within a quote. e.g.“Mary said ‘I like cats’ as she walked away.”

What we cannot agree on the following situation (for years):

  1. Dean's List ‘15 - ‘16
  2. Dean's List ’15 - ’16

It looks natural to use the opening single quotes as seen in example 1 but Microsoft Word autocorrects it to example 2.

So which single quote is the correct choice and why?

  • 2
    There's no such thing as an opening apostrophe. The symbol ’ is an apostrophe or a right closing quotation mark. The symbol ‘ is a left single quotation mark.
    – herisson
    May 4, 2016 at 2:50
  • 2
    This site suggests that the apostrophe is better than the single quotation mark: wordsintotype.typepad.com/blog/2009/12/they-.html
    – DyingIsFun
    May 4, 2016 at 2:53

2 Answers 2


In numbers that have been abbreviated, such as:

in the ’90s

Dean’s List ’15-’16

The apostrophe denotes the presence of abbreviation, much as in:

I’ll, let’s, where’d, can’t, ma’am, e’en, ...

’tis, ’em, ’cause, ...

There is also:

o’clock (for "of the clock"; according to the Online Etymology Dictionary)

I also found this Oxford Dictionaries article about the apostrophe, which even gives as an example:

pick ’n’ mix (short for "pick and mix")

  • You should include an example of a word where the omission is on the first or first few letters, as in 'cause (for because) and 'em (for them), since these are appropriately analogous to the case with years (where the first part is also omitted).
    – DyingIsFun
    May 4, 2016 at 3:11
  • @Silenus: Indeed. I've added a few more. Note that Wikipedia says that "'em" comes from "hem" rather than "them", but I think almost everyone assumes it comes from "them".
    – user21820
    May 4, 2016 at 3:35

As sumelic notes in a comment above, you need to use an apostrophe (’) when you are indicating the loss of part of a number or word, as with ’16 for the year 2016 or ’twixt for the word betwixt. The answer that user21820 provides covers this aspect of the question thoroughly, so I want to focus my answer on Microsoft Word's autocorrect behavior, which the OP mentions.

The autocorrect behavior arises from the fact that keyboards generally force the same unshifted key to do triple duty—as an apostrophe (’), as an open single quotation mark (‘), and as a single close quotation mark (’). In actual practice, this triple-dipping isn't a problem as long as your software program treats all three characters as neutral vertical marks ('). But by default, many word-processing programs (including the 800-pound gorilla Word) try to anticipate which of the three ways you intend to use that keyboard key, based on the adjacent keystroke choices you make.

So if you hit the ' key between two letter strokes—say, I and m—Word will infer that you want the ' keystroke to function as an apostrophe and will curl the character accordingly (’), yielding I’m. Likewise, if you hit ' after a letterspace and before a letter, Word will infer that you mean to start a quotation and will introduce an open quotation mark (‘); and if you hit ' after a letter but before a letterspace, it will infer that you want a close quotation mark (’) and will give you that.

But Word isn't smart enough to recognize situations where you want to use ' as an apostrophe after a letterspace (as with ’16 and ’twixt), so if you're using Word's default "smart" quotation mark preference, you have to trick Word into thinking that you're using the ' in a way that Word recognizes as appropriate for introducing a ’ rather than a ‘. Perhaps the simplest way to accomplish this (assuming that you don't have any smart apostrophes handy to copy and paste) is to type two letterspaces, then go back between them and type two apostrophes (which will turn into single open and close quotation marks), then type the 16 or twixt or whatever the word is that you want to precede with an apostrophe, then delete the letter space between the quotation marks and it, and then delete the superfluous open quotation mark:

As ‘’ 16 arrived, I looked ‘’ twixt the bars of my prison cell...

As ‘’16 arrived, I looked ‘’twixt the bars of my prison cell...

As ’16 arrived, I looked ’twixt the bars of my prison cell...

It sounds like a disproportionate amount of effort for such a simple result—and it is. But that's the price you pay for working with software that's smart but not smart enough.

Anyway, to return to your specific example,

Dean's List ’15 - ’16

handles the apostrophes correctly, and

Dean's List ‘15 - ‘16

does not, but you'll see the latter form occasionally (especially on websites) because the writers and editors responsible for the text (1) aren't aware that their software has turned the apostrophes into open quotation marks, or (2) don't recognize that ‘ is the wrong punctuation symbol to use in that situation, or (3) can't figure out how to outwit the software and get the result they want.

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