I own a Cannondale Super Six 105 (Ultegra now) Carbon 2012 bike and I can't stop the wobble in the headset. If I tighten down the top cap (with 6mm hex) I can get rid of the wobble (hands on the drops holding brakes - headset has a fair bit of play) but I cannot move the wheels freely with the handlebars. 

I stripped it down, cleaned it and assembled it again but its still wobbly after tightening the inner 5mm allen key.

Do I need [a new headset](http://www.cannondaleexperts.com/Cannondale-SuperSix-Complete-Headset--KP044_p_611.html) ? It's KP044 I think.

The bearings move around nice and easy but the compression ring feels very rough to touch.

The bike is 4 years old, 30,000+km cycled on it, I'm not sure whats wrong - 

(1) I didn't tighten properly 
(2) headset needs replacement or 
(3) bike is old and something wrong with frame. 

Would a new KP044 fix it for me or could the bike be kaput ? Also if I cycle on (1-2 weeks) with a wobble will it do damage to the frame ?

Some pictures
[![loosened these first](https://i.stack.imgur.com/3tvx3.png)](https://i.stack.imgur.com/3tvx3.png)

[![Spacers removed](https://i.stack.imgur.com/NOr3I.jpg)](https://i.stack.imgur.com/NOr3I.jpg)
[![sits like this](https://i.stack.imgur.com/fGs0P.png)](https://i.stack.imgur.com/fGs0P.png)
[![bearing](https://i.stack.imgur.com/YgleL.png)](https://i.stack.imgur.com/YgleL.png)
[![top cap](https://i.stack.imgur.com/Vt1xp.png)](https://i.stack.imgur.com/Vt1xp.png)
[![Compression ring - sits into bearing, feels rough](https://i.stack.imgur.com/CEHPU.png)](https://i.stack.imgur.com/CEHPU.png)

I don't know if the pictures are much of a help but everything is there except a bit of a rough corner feel.