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According to the sources I could find, Bulgaria was given a piece of land called 'Southern Dobruja' at the end of WW2 even though they officially were part of the Axis powers from 1941 up until 1944, when they were conquered by the Soviets. See Wikipedia: Bulgaria during World War II for a helpful map.

By modern history I mean since the industrial revolution.

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    I think losing side of the war is a poorly defined term: Bulgaria turned out to be in the Soviet sphere of influence - if we treat it as a part of the block, it was not the losing block; if we treat it as a country - it might have gained in territory, but lost in overall independence.
    – Roger V.
    Commented Aug 29, 2021 at 6:07
  • Don't forget that Bulgaria didn't join Germany in the Operation Barbarossa. Despite it actively fought on the German side (like in the Balkans) but it never invaded the USSR proper
    – d.k
    Commented Aug 30, 2021 at 10:04
  • @RogerVadim as if countries like Bulgaria (by their economy size, hence military might, influence etc. ever have 'independence'). Bulgaria was in Germany's 'sphere of influence', then it turned out to be in the USSR's one, then in the American one.
    – d.k
    Commented Aug 30, 2021 at 10:06
  • @DmitryKoroliov one could take this argument even further - the leading powers are not independent either, since their actions are more or less determined by those of their opponents: Germany was influenced by URSS and vice versa. The point is that one cannot consider territorial gain or loss independently of the more general context.
    – Roger V.
    Commented Aug 30, 2021 at 10:23
  • @RogerVadim No I meant another thing. You said that Bulgaria gained territory but lost its independence . What do 'leading powers' have to do with this statement? My point was Bulgaria didn't lose its independence since it had the same 'amount' of it as it had it in Germany's 'sphere' or in the USSR's or American 'sphere'. Romania was in the USSR's 'sphere' (and lost its independence according to you) yet it condemned the invasion in Afghanistan in 1979 and didn't boycott the LA Olympics in 1984.
    – d.k
    Commented Aug 30, 2021 at 10:39

2 Answers 2

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Examples of the losing side getting a net gain in land could be hard to find, but some countries got some land despite being in the losing side.

  • Spain was in the losing side in the Seven Years war. However in the treaty of Paris (1763) it got the Louisiana from France in exchange for having ceded the Floridas to Britain. Measured by area, that's a large net gain, although the value of those two territories could be more balanced.
  • The Ottoman Empire got some territory (Kars) from Russia at the end of World War I - although it lost way more land to the allies. However, it's debatable if that was the result of WWI or of the wars that followed it.
  • Austria got the Burgenland from Hungary, also at the end of Word War I. However it's debatable if this example qualifies because the losing participant in the war was Austria-Hungary which already had Burgenland and the whole Hungary.

I must admit that those examples are borderline cases for the conditions in the question, but I couldn't find anything better.

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  • Nice examples, but in fact they are borderline. Still good answer because you mentioned the limitations :) Commented Aug 30, 2021 at 18:31
  • Thanks for the example of Spain in 1763. Since that is a net gain, at least by acreage, and as I didn’t specifically mention the value of land, that does seem to be an answer. However 1763 would be a bit before the industrial revolution right?
    – M. Y. Zuo
    Commented Aug 30, 2021 at 23:24
  • That's what makes the case borderline. 1763 was before the industrial revolution in Spain, France and Louisiana, although by then the industrial revolution had already begun in Britain.
    – Pere
    Commented Aug 31, 2021 at 8:36
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The question is based on wrong premises: Bulgaria entered the war on the Axis side for many reasons, first of which being it gained territory on Romania (which was part of Axis as well).

Many reasons explained why Romania, under German pressure, accepted to lose territory to many countries: USSR, Hungary, Bulgaria. That is outside the scope of the question. But the point is that Bulgaria entered Axis for territory, and basically gained more by entering Greece's territory when the Germans attacked Greece.

But overall, compared to Romania, Bulgaria fought only a little. Romania and Hungary sent troops against USSR, Romanian troops fighting a lot and being aggressive against the population, for example at Odessa. Romania was probably the third participation to Barbarossa (after Germany and Finland). On the other hand, Bulgaria was a minor participation.

So when the USSR invaded Romania, Romania changed side and fought against Germany. But it was already invaded, while Bulgaria followed Romania example when Soviet forces were at its gates but not on its territory: thus Bulgaria was in better position to ask rewards for changing side than Romania, and that is why Bulgaria obtained the South Dobroudja.

So the premises of the question are wrong: Bulgaria was not a losing country that gained territory. It was a country changing side at the good moment to be on the winning side, so that it gained territory.

Now, do other examples exist? The answer is yes, but in particular circumstances: after the Yom Kippur war, Egypt regained Sinai while it has been beaten.

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  • Sorry, but sentences like 'Bulgaria entered Axis for territory' sound like they are from a fifth-grader's answer. Very primitive and probably far from reality
    – d.k
    Commented Aug 30, 2021 at 10:02
  • @DmitryKoroliov 1/ I explained in first sentence in detail that it was part of many reasons but the main one. 2/ "probably far from reality": no that is the reality. And as said in my answer, this is directly linked to what happened later 3/ you say I am far from reality: any argument for that? Commented Aug 30, 2021 at 18:31

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