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I found a couple of small online shops that sold copies of Diplomacy games used, but none that were great bargains. Because of that, and because none had more than one copy in stock (meaning that any listing I gave would be useless as soon as one person bought that item), I haven't included those stores here.
The best recommendation I can make for buying copies of the game used is to buy them at an online auction. The advantages of buying on auction is that if you are willing to accept a used copy of the game, you can generally (though not always) get a better deal than buying new. The other advantage is that if you are interested in specific versions of the game, you will rarely be able to find them except for used, and the easiest way to find them is on auction.
While Amazon.com, Yahoo!, and MSN all have online auctions, I've never seen the Diplomacy boardgame listed at any site other than Ebay so that's the one I am recommending (though it can't hurt to check the others).
At any given time, Ebay usually has around a dozen Diplomacy items for sale (sometimes more, sometimes less). The most common used Diplomacy item on Ebay is the 1976 Avalon Hill edition with plastic pieces. In addition to used editions, new ones come up periodically if you are willing to check back from time to time. Editions of Avalon Hill Diplomacy with wooden pieces come up relatively often, Colonial Diplomacy comes up for auction frequently, and Deluxe Diplomacy comes up from time to time as well. If you check back often, you will come across plenty of less common editions that come up, including older (1961 and 1971) editions by Games Research Inc., non-U.S. editions by Waddingtons/House of Games. Even less common, but still there from time to time, are U.K. editions of Diplomacy (more and more frequently is Ebay becomes more popular in the U.K.), copies of Machiavelli, and copies of the Gamer's Guide to Diplomacy. You can even occasionally find unopened copies of these older versions of Diplomacy, but if you are looking for unopened ones, it may take a bit of patience before one comes along and depending on the edition, they can get pricey compared to the used ones..
You can get a list of Diplomacy items on auction at Ebay via this link.
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