This happened to me on the battle server, I was picking up an arrow on my archer, and it made me drop my cudgel. I had to repair the cudgel 2x at the end.
I am assuming that if the item breaks when it's in your posession, you pay repairs. If you pick up another (or te same item) you can again pay repairs on it.
This is the only time I have EVER paid double repairs on an item.
Oh, and I have paid item repairs (on battle, again) for an item I no longer had (traded my pike for a lance, and got on a horse) and also for the horse in the same round.