San Marino has participated in the Eurovision Song Contest five times, debuting in the 2008 contest, followed by participation in 2011, 2012 and 2013. Having failed to qualify in their first four attempts, San Marino qualified for the Eurovision final for the first time in 2014. Valentina Monetta represented San Marino in 2012, 2013 and 2014, making her the first singer to participate in three consecutive contests since Udo Jürgens, who competed in 1964, 1965 and 1966 for Austria.
The first Sammarinese entry in the Eurovision Song Contest was Miodio, with the Italian language song "Complice". San Marino holds the honour of being the 50th country to participate at Eurovision, participating 5th in the first semi-final of the contest. However, Miodio failed to qualify for the final, receiving just 5 points in total and coming last. Despite this, the winner of the 2008 contest, Dima Bilan, concluded his "Winner's Tour" in San Marino. SMRTV broadcast the full event.
SMRTV had originally planned to compete at the 2009 contest in Moscow, Russia. The Sammarinese Minister of Culture announced shortly after the 2008 contest that they "have good hopes to return". SMRTV announced that it would be reviewing the 2008 contest, and would have a decision on 2009 participation by the end of the year. It was then rumoured that the country would not be participating in the 2009 contest, following rumours that SMRTV would withdraw due to poor results at the 2008 contest, however SMRTV rebuked the claim and confirmed its interest in the 2009 contest. In the end, SMRTV announced its withdrawal from the 2009 contest, having already applied to enter. The broadcaster insisted that this was not due to the poor results of the previous year, but financial difficulties faced by SMRTV.
SMRTV made an application to participate in the 2011 contest, which was later confirmed. It was the second participation in the ESC for San Marino. The singer Senit was announced as the Sammarinese entry at the Eurovision Song Contest 2011, which was held in Düsseldorf, Germany. She sang "Stand By", performed in English. As in 2008, SMRTV broadcast the full event. For the second time, San Marino failed to qualify for the final, coming sixteenth out of nineteen countries, with 34 points.
On 17 January, it was confirmed by the EBU that San Marino will be participating in the 2012 edition. SMRTV confirmed on 14 March, that Valentina Monetta would represent San Marino in the Eurovision Song Contest 2012 in May. She was internally selected by SMRTV. "Facebook Uh, Oh, Oh" was presented as the Sanmarinese entry. However, it was announced that the song's lyric breached rule 1.2.2.g of the competition (prohibiting "commercial messages of any kind"), which resulted in the lyric being disqualified. The lyric and the title of the song were changed shortly afterwards to The Social Network Song (Oh Oh - Uh - Oh Oh). Monetta performed the song during the first semi-final, but failed to advance to the final. Together with Montenegro, the song was expected to finish either last or second to last, but after the full results were revealed after the final on 26 May, it was revealed that the song ended in 14th place with 31 points, making the entry San Marino's best placing in Eurovision compared to previous years.
San Marino confirmed in November 2012 that they would participate in the 2013 contest. Artist Lys Assia had been rumoured to represent the country with her song "All in your head" which failed to make the national final of Switzerland, but this was later denied. Instead, at a press conference in January 2013, Valentina Monetta was revealed as the choice to represent San Marino at the Eurovision Song Contest in 2013. She performed the song 'Crisalide (Vola)' in the second semi-final on 16 May in Malmö. For the fourth time, San Marino failed to qualify for the final, despite being, unlike previous year, a fans' favourite (2nd place for OGAE). However, Monetta scored the best result for San Marino; 11th place in the semi-final with 47 points.
On 19 June 2013, SMRTV San Marino confirmed they had signed a pre-agreement with Valentina Monetta to represent San Marino at the Eurovision Song Contest 2014 for the third time. This made Monetta the fourth singer to represent a country in three consecutive Eurovisions after Lys Assia for Switzerland and Corry Brokken for the Netherlands, both in the years 1956, 1957 and 1958 and Udo Jürgens for Austria in 1964, 1965 and 1966. She qualified from the first semi-final took the 10th place with 40 points with the song Maybe(Forse), just one point ahead of Portugal. In the Grand Final Monetta performed as number 25 and placed 24th with 14 points.