Ranked 210th in the world by FIFA, the European minnows have defied all the odds to finish top of League D Group 1 with seven points from four games, one point ahead of Gibraltar in second and five clear of Liechtenstein at the bottom of the three-team group.
Since gaining affiliation to FIFA and UEFA in 1988, San Marino have suffered defeat in 199 of the 211 fixtures they have contested and have conceded 10 or more goals in seven of those matches.
La Serenissima's first-ever victory in a friendly against Liechtenstein (1-0) back in 2004 was followed by a 20-year winless streak in all competitions, but they have since celebrated two memorable triumphs in the space of just three months under head coach Roberto Cevoli.
The 55-year-old, who managed a number of lower-league Italian clubs before taking the reins of San Marino last year, steered his current side to their first-ever Nations League win in September - another 1-0 victory over Liechtenstein, who are ranked 200th.
San Marino create history with comeback win over Liechtenstein
San Marino also rescued a point in a 1-1 home draw with Gibraltar last Friday, scoring a 90th-minute equaliser, before claiming their biggest-ever victory and the first away win in their history against Liechtenstein on Monday.
Indeed, San Marino scored more than once in a competitive match for the first time, while their win over Liechtenstein is the first time they had ever scored three goals in any game.
The landlocked nation of just over 30,000 people surrounded by north-eastern Italy were forced to come from behind to secure maximum points for the first time, after Liechtenstein took the lead in the 40th minute when Aron Sele fired a strike in from outside the penalty box.
San Marino needed just 50 seconds after the interval to restore parity, though, with Lorenzo Lazzari bursting in behind to meet a ball over the top before making the net ripple with a powerful finish.
Cevoli's side then took the lead in the 66th minute when Nicola Nanni rolled a composed penalty into the bottom corner, sending Lichtenstein goalkeeper Benjamin Buchel the wrong way.
'San Marino have shown what they are worth'
Ten minutes later, Alessandro Golinucci fired home a sweetly-struck first-time effort from 10 yards, sparking wild celebrations from his teammates and ultimately securing a historic victory for the European minnows.
Nanni is now San Marino's joint-second top scorer with three goals, level with Filippo Berardi, while Lazzari and Golinucci are now two of only six players to net more than once for their country.
"Finishing that first half 1-0 down was an insult to football, but the boys were brilliant and deserved what they've managed to achieve," Cevoli told reporters after the match.
The president of San Marino's Football Federation, Marco Tura, added: "These boys made history tonight. As people, as athletes, as men they have shown what they are worth. I cried with the boys."
San Marino have been rooted to the bottom of the FIFA World Rankings since November 2023 and they will be eager to find out if their two wins in six matches will be enough to move then above Anguilla when the standings are updated on November 28.