For me, the greatest CLOD moments are on the ATAG server, i. e.:
Returning home in a 109 or 110 from a successful mission over England with hardly any fuel and no ammunition left, but a Spitfire in my six. And then, in the very last second, looking behind me and spotting the beautiful cannon rounds from another 109 tearing the Spitfire apart. Especially, if this 109 followed my support request on Teamspeak.
Of course, saving a friendly plane from certain death is also quite satisfying.