Inscribed along the border, starting at the bottom left it says "FOR TWO YEARS CONTINVOVS SERVICE ON THE PANAMA CANAL" (note the Roman style lettering which renders the letter "U" as "V"). Along the bottom border, with a divider on either side is the recipient's name. The center of the medal has a three-quarter bust of President Theodore Roosevelt. Near the bottom of the bust in the field on the right in small letters is the name of the designer "V.D. BRENNER". The medal has a loop attached on either side of the top.

Attached to the medal by the two loops are the two year bars. In this case there will be four two year bars. The bars are somewhat rectangular with arrows on either side. The middle of the bar says "TWO YEARS" in large letters. The arrows are ornate with a fan-like design in each arrow. The top and bottom of each arrow has a small hole, for a total of four holes (two at each end). The bar has a raised edge along the rim and around each hole. One-link chains on either side go through these holes and attach the bars to the medal below, the header above and to the other bars.

The header piece is attached to the top of the uppermost bar. The header is somewhat oval shaped with a middle point. It has an ornate line design on it which features s-curves and looped lines. The bottom of the header has two small holes, used to attach the header to the uppermost bar.

Inscribed along the border, starting at the bottom left it says "PRESENTED BY THE PRESIDENT OF THE VNITED STATES" (note the Roman style lettering which renders the letter "U" as "V"). Along the bottom border, with a divider on either side is "N^o" and the medal serial number, some space, and then the years of service. The center of the medal has a bird's eye view of the finished Culebra Cut, steamers passing through, Gold Hill on the left and Contractor's Hill on the right. Above the horizon is the motto "THE LAND DIVIDED THE WORLD UNITED". In the bottom center appeared the shield of the Canal Zone showing a Spanish Galleon going through the canal.

The back of the two year bars are plain. They are engraved with the "N^o", the two year bar serial number and then the years of service. Note that the font size used for the engravings varied from year to year.

The back of the header is plain, but features a hinged pin for attaching the medal to the owner's clothing.

President Theodore Roosevelt and his wife spent three days on the Isthmus in mid-November 1906, to inspect the building of the Canal. This was the first time a President of the United States had traveled outside the country while in office. On the evening of November 17th from a bandstand in Panama, President Roosevelt announced "I shall see if it is not possible to provide some memorial, some mark, some badge, which will always distinguish the man and woman who, for a certain space of time, had done his work well on the Isthmus." Upon his return to the United States, President Roosevelt proposed to congress that they recognize the Canal Diggers with the award of a medal. It was given to all American citizens who had at least two years of satisfactory continuous service with the Canal construction forces or the Panama Railroad between May 4, 1904 and December 31, 1914. For each additional two years of service, a bar was given to the medal holder. Work on the canal (under the French) before May 4, 1904 did not qualify, nor work as a non-citizen of the United States, nor did military service in the Canal Zone. This was a strictly civilian award, and if it was earned by military personnel while a civilian, was not to be worn on their uniform.

The medal was designed in November 1908 by F.D. Millet, an artist who later went down with the S.S. Titanic. Victor D. Brenner was the "medalist" who prepared the plaster model and apparently finalized the design. It is his name that appears on the medal next to the portrait of President Roosevelt. Victor D. Brenner and President Roosevelt became friends while President Roosevelt was sitting for his likeness for the Roosevelt Medal. Both men shared a great admiration for Abraham Lincoln, so President Roosevelt commissioned the young sculptor to design a new cent commemorating the 100th aniversary of Lincoln's birthday. That design was used for the 1909 Lincoln cent. Brenner's design for the cent reverse was used until 1958, and his design for the obverse is still in use to this day. The engraving on the medals and bars was done by Mr. Alva Nelson of New York City.

Bronze scrap metal in the form of staybolts from the equipment abandoned on the Isthmus by the French was used in making these bronze medals. The February 1909 Canal Record announced that 1000 pounds of French scrap had been sent to the Philadelphia Mint for this purpose. Later it was noted that the 1000 pounds was sufficient for all the medals and bars that were minted.

The first batch of 2264 medals and bars covering service between May 4, 1904 and the end of 1908 arrived in Panama on September 3, 1909 on the steamship Colon (according to The Canal Record). Distribution of the medals began immediately.

A total of 7,423 medals were struck of which 7,391 were issued. The balance were reserved as replacements for recipients who lost their original medal.

The Roosevelt Medal was also commonly referred to as the Panama Service Medal and Isthmian Canal Medal.