The hosts are under new management in the midst of an 11-match losing run, while their visitors most recently fell short in the CONCACAF Nations League.
Match preview
San Marino will play their first match of the new year on Wednesday under new stewardship, as they continue their search for a first victory since 2005.
Indeed, Roberto Cevoli took the reins in December after Fabrizio Costantini's two-year tenure came to an end, culminating in a tough Euro 2024 qualifying campaign in which La Serenissima failed to earn a point.
The lowest FIFA-ranked nation suffered defeats in each of their eight matches, albeit fighting valiantly in many of those, having only lost 2-1 at home to Denmark in October and concluded with a 2-1 home defeat to Finland in November, having pulled a goal back through Filippo Berardi late on after Pyry Soiri's second-half brace.
Those results stretched a losing run to 11 matches, since La Serenissima were able to play out a 1-1 draw with Saint Lucia in a friendly in late 2022, while April will mark the 20-year anniversary of their only ever victory thus far against Liechtenstein.
Now hoping for a fresh start under the new management of Cevoli with a run of friendlies looming before the beginning of the UEFA Nations League campaign in September, San Marino will look to end their wait for a historic win in Wednesday's friendly on home turf.
They meet a Saint Kitts and Nevis team who will also play their first football on 2024 in the upcoming pair of friendlies in San Marino after last being in action in November.
The visitors' last friendly came in early 2022, and they have since had a busy schedule across two CONCACAF Nations League campaigns and a CONCACAF Gold Cup last year.
Their latest Nations League term began in September, but the Sugar Boyz were unable to progress from League B Group A, finishing at the bottom of their division with four points from six outings, courtesy of a 3-2 win away at Sint Maarten thanks to Tiquanny Williams's hat-trick and a goalless draw at home to Saint Lucia, before the campaign culminated in a 5-0 thrashing at the hands of Guadeloupe.
Now travelling to Europe for this week's friendlies before kicking off World Cup Qualifying in June, Saint Kitts and Nevis will bid to return to winning ways in Serravalle on Wednesday with what would be a seventh victory in 18 matches under Austin Huggins's tutelage.
San Marino form (all competitions):
L
L
L
L
L
L
Saint Kitts and Nevis form (all competitions):
L
L
W
L
D
L
Team News
We are yet to see how Roberto Cevoli will line San Marino up, but captain and veteran Matteo Vitaioli is bound to again lead the attack having earned a record 91 caps for La Serenissima thus far.
He could be joined by key man Filippo Berardi, who had to settle for a substitute appearance in their narrow defeat to Finland last time out, while Lorenzo Lazzari may offer further attacking support from the midfield.
The experienced duo of Alessandro Golinucci and Marcello Mularoni will likely continue in the engine room, while Mirko Palazzi remains a key man at the back with 74 caps to his name.
Austin Huggins tends to line Saint Kitts and Nevis up in a 4-4-2 shape, and Harry Panayiotou is bound to lead the line, having notched up 11 international goals in his 34 Sugar Boyz caps thus far.
With Tiquanny Williams absent from the squad, 19-year-old Diego Edwards could again join Panayiotou up front, while Raheem Somersall and Omari Sterling-James will look to cause problems on the wings.
Cardiff City's Romaine Sawyers is a key man in midfield, having earned 43 caps and contributed six goals, while centre-back Andre Burley will again feature in front of experienced stopper Julani Archibald.
San Marino possible starting lineup:
Benedettini; D'Addario, Franciosi, Rossi, Palazzi, Tosi; Golinucci, Mularoni, Lazzari; Berardi, Vitaioli
Saint Kitts and Nevis possible starting lineup:
Archibald; Hanley, Burley, Williams, Shade; Sterling-James, Sawyers, Terrell, Somersall; Edwards, Panayiotou