How do I create vertical table headings in confuence

Here's a start for you...

Wrap the table you want with a rotate-headers user macro.

Here's the code:

## Macro: rotate-table-headers
## Macro title: A macro for rotating all the headers in a table
## Macro has a body: Y
## Body processing: n/a
## Output: HTML
##
## Developed by: David Simpson <[email protected]>
## Date created: 2013-11-20
## Installed by: My Name

## @param height:title=Height|type=string|required=true|desc=e.g.100px


<style>
    /** @see: http://css-tricks.com/snippets/css/text-rotation/ */
    .rotate-headers th div.tablesorter-header-inner {
        -webkit-transform: rotate(-90deg);
        -moz-transform: rotate(-90deg);
        -ms-transform: rotate(-90deg);
        -o-transform: rotate(-90deg);
        transform: rotate(-90deg);

        filter: progid:DXImageTransform.Microsoft.BasicImage(rotation=3); /* Internet Explorer */
    }
    .rotate-headers th {
        vertical-align:middle;
        height: $paramheight;
    }
</style>

<div class="rotate-headers">$body</div>

It produces something similar to this:

You may have to alter the CSS somewhat, but its a good start.