Use Word 2010's Numbering feature in tables and make it automatically number multiple table columns vertically. This way, each cell in each column will be placed under the correct number.

A number of readers have asked how to divide text into columns in Microsoft Word.Well, there are four basic column types that I call “Book,” “Newspaper,” “Table”… ...

While Word's generated formats are numbers only, you can update and customize a table of contents with your own text. Add text such as "page" before the numbers or other entries such as "see page ...