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East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

Most of those parts of Germany that became part of Poland and Russia after WWII saw a steep decline of population in the first years after 1945, but at least the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were before the war.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.

Abkhazia had a population of 380 000 in 1950, peaked above 500 000 in the 1980s and is below 250 000 now. Karabakh and surrounding territories (those occupied by Armenia until recently) might be similar, but I think it would be harder to find pre-1950 data because those areas contain parts from multiple administrative units.

East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.

Abkhazia had a population of 380 000 in 1950, peaked above 500 000 in the 1980s and is below 250 000 now. South Ossetia's population is also considerably less now then it was in 1939. However, in neither case I am really sure whether the population numbers are for the same area. One might suspect current lines of military control are not wholly equal to Soviet-era administrative boundaries. And both regions do not really fit your size criteria.

One might suspect the pattern of population decline is quite similar in Karabakh if we include the surrounding areas that were occupied by Armenia until recently. However, in this area I am reasonably certain that lines of military control did not follow administrative boundaries from previous censuses.

I initially had suspected that those parts of Germany that became part of Poland or Russia after WWII* had also not fully caught up with their pre-war population numbers, but looking at the population numbers from this fairly official German site and current population numbers of roughly similar Polish administrative units today that does not really seem to be the case. Or at least it is not obvious. And the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were before the war.

_{*i.e. East Prussia, almost all of Silesia, most of Pomerania, and Eastern Brandenburg}

East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

Most of those parts of Germany that became part of Poland and Russia after WWII saw a steep decline of population in the first years after 1945, but at least the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were before the war.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.

East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

Most of those parts of Germany that became part of Poland and Russia after WWII saw a steep decline of population in the first years after 1945, but at least the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were before the war.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.

Abkhazia had a population of 380 000 in 1950, peaked above 500 000 in the 1980s and is below 250 000 now. Karabakh and surrounding territories (those occupied by Armenia until recently) might be similar, but I think it would be harder to find pre-1950 data because those areas contain parts from multiple administrative units.

East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

Most of those parts of Germany that became part of Poland and Russia after WWII saw a steep decline of population in the first years after 1945, but at least the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were back then.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.

East Germany (the former GDR) had a steady population decline since the 1950s which continues until today. They started with about 18.5 million in 1950 and had about 16.5 million in 1989. In 2015 the area had about 14 to 14.5 million inhabitants (own calculation, assuming 1.5 to 2 million inhabitants in the Eastern part of Berlin and neglecting smaller border changes e.g. in Weststaaken or Amt Neuhaus).

Berlin itself had a population of 4.3 million in 1939, 3.4 million in 1989 and is at about 3.7 millions today.

Most of those parts of Germany that became part of Poland and Russia after WWII saw a steep decline of population in the first years after 1945, but at least the major cities (e.g. Szczecin, Wrocław, Gdańsk, Kaliningrad) are not smaller now than they were before the war.

The Czech republic today seems to have a (very very slightly) smaller population today than Bohemia and Moravia had in 1930.