Steve Clarke's squad have faltered since securing back-to-back qualifications for the European Championship, while their opponents conceded some 20 goals across their final two qualifiers.
Match preview
Having won five successive Euro qualifiers last year, to finish second in Group A and secure an automatic place in Germany, Scotland were feeling bullish about their prospects of making a major impact on the continental finals.
After toppling Spain, the Tartan Army drew plenty of acclaim, but a subsequent downturn in results has left them in need of a morale boost during this month's warm-up friendlies.
In March, they suffered a heavy loss to the Netherlands in Amsterdam, then slipped up against neighbours Northern Ireland: the latter 1-0 loss at Hampden leaves Steve Clarke and co on a seven-game streak without victory.
That represents Scotland's worst winless run since 2008, and a tally of 19 goals conceded across those seven matches has caused concerns about how an injury-hit squad will fare this summer.
Losing to their regional rivals on home turf also means that the Tartan Army have now won just one of their last 13 friendly fixtures, being beaten each of the last five, and that trend surely cannot continue on Monday.
Following a final tune-up against Finland on Friday evening, the Scots will hone in on their Group A tussle with Hungary, Switzerland and Germany at the Euros, where they meet the hosts in Munich for the tournament opener.
After being hammered 14-0 by ruthless France and then losing 6-0 to the Netherlands on home soil, Gibraltar's dismal end to European Championship qualification left them in no frame of mind to tackle their UEFA Nations League playout in March.
Los Llanis met Lithuania to determine who would drop down into League D, and 1-0 defeats in both legs resulted in relegation for the squad overseen by Uruguayan head coach Julio Cesar Ribas.
Therefore, they must meet fellow minnows San Marino and Liechtenstein in the next Nations League - albeit one World Cup qualifying playoff place will be available to the overall League D winners.
With 12 games since the start of 2023 bringing 12 defeats, zero goals and 48 conceded, the outlook may seem grim, but back-to-back matches in Faro now offer a chance to turn the page.
Once they have met Scotland, Gibraltar will play Wales on Thursday, and avoiding defeat in either contest would represent a major achievement for the tiny Mediterranean nation.
Gibraltar form (all competitions):
L
L
L
L
L
L
Scotland friendly form:
L
L
Scotland form (all competitions):
L
L
D
D
L
L
Team News
After Lyndon Dykes was stretchered off during training on Friday, Scotland manager Steve Clarke may have to add his first-choice striker to a long injury list.
Dykes - who has scored nine times in 36 internationals and played in all eight Euro qualifiers - could now join Bologna captain Lewis Ferguson and full-back duo Aaron Hickey and Nathan Patterson on the sidelines.
In the latter pair's absence, Bristol City's Ross McCrorie competes with Celtic defender Anthony Ralston for selection on the right, while several other places are subject to fitness.
Stuart Armstrong and John Souttar both missed the end of the season with their respective clubs; uncapped teenager Ben Doak only recently resumed training at Liverpool following knee surgery, and Ryan Jack has barely featured for Rangers.
Meanwhile, Gibraltar have injected fresh blood into their squad by calling up six players without a senior cap, including Chesterfield winger Liam Jessop.
The 18-year-old joins Manchester United youngster James Scanlon among a number of attacking options available to Julio Cesar Ribas.
Nonetheless, regular starters such as Tjay De Barr, Liam Walker and 42-year-old veteran Lee Casciaro are all expected to line up at Estadio Algarve.
Gibraltar possible starting lineup:
Coleing; Jolley, Sergeant, Mouelhi, Olivero, J. Chipolina; Walker, Pozo, De Haro, Casciaro; De Barr
Scotland possible starting lineup:
Gunn; McCrorie, Hendry, Porteous, Robertson; McTominay, Gilmour; Forrest, McGinn, Christie; Adams
We say: Gibraltar 0-3 Scotland
In the nations' third meeting since Gibraltar joined UEFA, Scotland will avoid embarrassment and secure a long-awaited victory to end their worrying winless run.