Australia
Surely not the smallest country in terms of size, but given its small population, which is half of that of South Korea, Australia qualifies to be on the list. Australia have won a massive 467 Olympic medals, making it the 10th richest country in the list.
The country has 138 Gold medals apart from 153 Silver and 176 Bronze medals. The country failed to win a Gold in 1976 and it was considered a national embarrassment. Subsequently, Australian Institute of Sports was instituted in 1980 and the results were for everyone to see when Australia ended 2000 Olympics with 58 medals.
Australia has produced some of the best swimmers in Ian Thorpe, Dawn Fraser, Murray Rose and Libby Tricket and has dominated field hockey as well.