10. Mali (11 Summer Olympiads)
Mali started competing at the Olympics in 1964 with the Summer Olympics in Tokyo, Japan. Most all of Mali’s athletes have fallen into the Did Not Advance territory, and were essentially out after the first preliminary match-up. However, the high-water mark of Malian international athletic ascendancy came in the 2004 Summer Olympics in Athens, Greece. The Malians made it to the quarterfinals in soccer. The underdog African team managed to hold powerhouse Italy scoreless until four minutes to go in the game, when Italy scored their lone goal to advance. It was a heroic effort by a plucky team.
9. Liberia (12 Summer Olympiads)
The Liberian Olympic History started in 1956 in Melbourne, Australia. In the 1980 Games in Moscow, the Liberians actually withdrew immediately after the Opening Ceremonies. After the 1988 Games in Seoul, Korea, Liberia sent its athletes off with a magnificent ceremony. After their poor showing in the Games, two athletes were actually assaulted and physically beaten. Liberia has never managed to advance in any sport beyond a preliminary at the Games.
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8. Madagascar (11 Summer Olympiads, 1 Winter Olympiad)
Madagascar also started their Olympic Medal drought in 1964 with the Summer Olympic Games in Tokyo, Japan. Jules Randrianari did manage to give some pride to the Madagascar team in 1980, by finishing 25th in the Marathon event at the Moscow Games. In 2006, Madagascar made its first appearance at the Winter Olympics in Turin, Italy, when Mathieu Razanakolona (its only representative) finished 39th in the Men’s Giant Slalom. Razanakolona, however, did not finish the Men’s Regular-Sized Slalom that same year.
7. Malta (15 Summer Olympiads)
Malta competed in the Olympics for the first time at the 1928 Summer Games in Amsterdam, Netherlands. Malta is notable for being the only European member of the International Olympic Committee to have never participated in the Winter Games. Not that the Summer Games have gone noticeably better for the Maltese. The 1980 Summer Games in Moscow were the first to feature archery. Malta got in on the front end, hoping to establish some credence in at least one sport. They sent one male and one female Archer as their only entrants in the Games. Leo Portelli finished dead last in the competition. Joanna Agius did a little better…finishing next-to-last.
6. Nepal (12 Summer Olympiads, 3 Winter Olympiads)
Nepal also started their Olympic History with the 1964 Summer Games in Tokyo, Japan. Nepalese athletes have not managed to fare well in either the Summer or the Winter Games. As a matter of fact, finishes in the upper half of the top fifty are fairly rare. In this culture, Bharat Sawad finishing 22nd in the Summer Olympics in Seoul, for the flyweight event in weightlifting, should be nearly statue-worthy. Nepal does get some credit for being lovable losers in both the Summer and Winter Olympics, as well as consistently competing in the games.
5. Myanmar (16 Summer Olympiads)
Myanmar’s history in the Summer Games has so far stretched from the Games in 1948 in London, England, to the 2012 Olympic Games in…well, also London. Myanmar has the curious distinction of having lost at the Olympic games from 1948 – 1992 as Burma. The name was officially changed to Myanmar for the 1992 games, yet the losing has continued for the last twenty years. In 2004, Thin Thin Khaing brought pride at drama to the Women’s Archery Competition in Athens, Greece. Khaing was eliminated, but had the only archery round ever to force a record three tie-breaking shots.
4. Bolivia (13 Summer Olympiads, 5 Winter Olympiads)
Bolivia’s first Summer Olympics occurred in 1936 in Berlin, Germany. Bolivia would then take a 28-year hiatus until the 1964 Games in Tokyo, Japan. María Teresa Monasterio had Bolivia’s highest finish in any sport, with a 17th place finish in Beijing in women’s weightlifting. Montasterio impressively managed to make this competitive finish at the somewhat advanced age (for Olympic athletes) of 38. Bolivia has not participated in the Winter Games since 1992.
3. Andorra (10 Summer Olympiads, 10 Winter Olympiads)
Andorra has appeared in every Olympics Games (both Summer and Winter) since 1976. Andorra’s first Olympic appearance was the Winter Games in Innsbruck, Austria. While the consistency effort is certainly laudable, the results have certainly been a bit lacking. The lone top-20 finish for any athlete by Andorra came in the 1988 Winter Games in Nagano, Japan. Vicki Grau finished 19th in the Women’s Slalom. The same year, Grau did not finish the Women’s Giant Slalom. That would be the high-water, or perhaps high-snow, mark.
2. San Marino (13 Summer Olympiads, 7 Winter Olympiads)
San Marino first participated in the Summer Olympic Games in 1960 in Rome, Italy. San Marino was somewhat notable for causing a bit of a stir about the United States-led boycott in the 1980 Moscow Summer Olympics. San Marino supported the boycott, partially. San Marino allowed its athletes to compete, but the San Marino contingent did not compete under their own flag in support of the boycott: they competed under the Olympic flag. They might want to use the Olympic flag more often. Stefano Casali had one of San Marino’s best finishes ever, with a 24th place finish in the 20-kilometer walk.
1. Monaco (20 Summer Olympics, 8 Winter Olympics)
Monaco started its long march toward being the country competing in the most Olympics without an athletic medal in 1920. The 1920 Summer Olympics were held in Antwerp, Belgium. Monaco’s Julien Médecin did actually win a Bronze Medal in the 1924 Games…for Architecture. The medal was for Town Planning for the Stadium of Monte Carlo. Since art competitions are not counted in the official athletic medal count, Monaco still does not officially have a medal in an athletic competition. The only question now is, what will happen first: Monaco winning an athletic medal, or the Chicago Cubs winning the World Series?