Portugal cruised to a 3-1 friendly win over Scotland at Hampden Park as debutant Helder Costa, Eder and Bruma piled the misery on Alex McLeish.
Defeat to Fernando Santos' side follows a woeful reverse against Israel on Thursday and means that McLeish has now lost six of his eight games in charge since taking the top job for the second time in February.
After a largely even opening period, Portugal – who made 10 changes from the side that beat Poland 3-2 on Thursday – took the lead in the 43rd minute, Wolves striker Costa turning home Kevin Rodrigues' low cross from close range.Eder and Bruma struck in the closing 16 minutes to ensure that Steven Naismith's neat strike deep into stoppage time was nothing more than a consolation goal for the hosts.
After a tepid opening, Scotland almost took a fortuitous lead after 14 minutes. James Forrest's deflected cross caused havoc in the Portugal penalty area and only a smart save from Beto prevented Sergio Oliveria's wayward header from finding his own net.
At the other end, Bruma flashed an effort agonisingly wide of Craig Gordon's left-hand post midway through the first half as the visitors belatedly woke from their slumber.
Portugal's more positive approach was rewarded two minutes before the interval when Costa stole in ahead of Andrew Robertson to prod home from six yards.
Scotland should have pulled level shortly after the restart, but an unmarked Scott McKenna inexplicably headed wide from John McGinn's corner.
They were made to pay for that miss in the 74th minute when Eder met substitute Renato Sanches' lofted free-kick to head past Gordon.
Bruma added a third six minutes from time, cutting in from the left and firing into Gordon's far post, but Hearts striker Naismith had the final say, curling in after latching onto Gary Mackay-Steven's pass.
What does it mean: McLeish's woes continue
Things have not gone to plan for McLeish since his return to the Scotland hot seat. They were second best to Portugal's second string and serious questions will now be asked of the former Rangers and Birmingham boss. Portugal, meanwhile, look in rude health and can toast a third win on the spin.
Costa makes his mark
He has yet to find the net for Wolves in the Premier League so far this season, but the 24-year-old made no mistake with his first international goal, showing superb hunger to nip ahead of Robertson for Portugal’s opener.
McKenna's miss proves costly
The Aberdeen man could have given Scotland the platform to go on and get a result from the game had he buried his header shortly after the restart. As it was, it flashed wide and Portugal clinically punished the young defender.
Key Opta facts:
- After going seven games without defeat between March and October 2017 (W4 D3), Scotland have since lost seven of their last nine games in all competitions (W2).
- Portugal have won each of their last three internationals, as many as they had in their previous 11 games before this run (D6 L2).
- Scotland are winless in their last six games against Portugal in all competitions (D2 L4), scoring just two goals in total across these meetings.
- Scotland have kept a clean sheet in just two of their eight games since Alex McLeish returned as manager (13 goals conceded in total).
- Steven Naismith has scored in each of his last two appearances for Scotland at Hampden Park, having also netted against Albania last month.
- Helder Costa's opener was his first goal for Portugal, on what was his first senior appearance for the national team.
Both sides resume their Nations League campaigns on November 17. Scotland travel to Albania, while Portugal will visit Italy.
|Sharapova stunned by Barty as Kvitova takes Anisimova to school|
|Guardiola demands improvement after Man City win|
|Sexton has bat phone to referees - Jones|
|Alonso accepts Chelsea guilty of ´silly mistakes´ in Arsenal defeat|
|Guardiola woke us up - Sane reveals half-time rocket for Man City|
|A first step to something bigger - Tsitsipas eyeing glory after shocking Federer|
|Thailand 1 China 2: Gao Lin keeps dream alive for Lippi|
|Tsitsipas in dreamland after ousting Federer, birthday boy Tiafoe breaks new ground|
|Huddersfield Town 0 Manchester City 3: Danilo, Sterling and Sane on target for ton-up City|
|Allegri: Khedira will be like a new signing for Juventus|
|Manchester City reach 100 goals in 2018-19|
|Australia v Uzbekistan: Leckie´s return is ´like a new signing´, says Arnold|
|Jordan 1 Vietnam 1 (aet, 2-4 on penalties): Keeper Van Lam the shoot-out hero|
|Federer confirms French Open return after Melbourne exit|
|I accept his decision - Gattuso axes Chelsea-bound Higuain|
|The rapid rise of Federer-conqueror Tsitsipas|
|Gracious Federer hails ´better player´ Tsitsipas after Australian Open exit|
|Tsitsipas ´happiest man on earth´ after stunning Federer|
|Harden focused on wins, not personal feats after scoring 48 points|
|PSG midfielder Verratti suffers sprained ankle|
|Inspired Tsitsipas dethrones Federer|
|PSG´s Cavani considering career finale in Uruguay|
|Feisty Collins ready to make more noise after thrashing Kerber|
|I´ve got to work on my soccer skills! - Mavs´ Doncic didn´t know ejection rule|
|Lakers won´t rush LeBron & Rondo back despite Ball injury|
|A-League Review: Victory fightback in thriller with Wellington|
|Henry explains foul-mouthed confrontation with Strasbourg´s Lala|
|Nadal wary of ´dangerous´ Tiafoe|
|Emery ´not positive´ over Bellerin injury|
|Harden scores 48 points as Rockets rally past Lakers in OT|
|Pacquiao wants Mayweather rematch after beating Broner|
|Sharapova unimpressed with questions after Melbourne exit|
|Nadal outclasses Berdych en route to quarters|
|Collins trounces 2016 Aus Open champion Kerber|
|Sanchez: Man United thriving thanks to Solskjaer|
|Sharapova crashes out of Australian Open|
|Devils´ Palmieri replaces Hall on NHL All-Star roster|
|Tuchel stunned by PSG´s nine-goal thrashing of Guingamp|
|Modric wants to extend Real Madrid stay|
|Marotta: Icardi will re-sign, Godin wants Inter|
|´F*** no!´ - Westbrook on if he´s cool with Embiid|
|Mickelson shoots 66 to stay ahead at Desert Classic|
|Real Madrid? You never know what the future holds - PSG´s Mbappe|
|Inter lacked quality in disappointing Sassuolo draw - Spalletti|
|Walton has one goal for Lakers-Rockets matchup: Keep Harden under 50 points|
|CAF Champions League Review: Simba learn Vita lesson as Sundowns find form|
|Bayliss relishing pressure of World Cup and Ashes to finish England reign|
|Guardiola keen to keep City rhythm and challenge on four fronts|
|Fifita backs Johnson to inspire the Sharks|
|For Real Madrid, nothing is impossible - Solari refuses to give up in title race|
|Inter 0 Sassuolo 0: Spalletti´s side labour at sparse San Siro|
|Marshawn Lynch will continue playing ´if it works out´|
|Simeone excited by improving Atleti|
|Jones ´cautiously optimistic´ over Farrell ahead of Ireland clash|
|Sarri questions Chelsea motivation after Arsenal surrender|
|Emery urges Arsenal to find balance after downing Chelsea|
|Koscielny hails Arsenal fighting spirit in Chelsea win|
|Pellegrini: It was not a good idea for Arnautovic to play|
|Iran v Oman: We´re not satisfied yet, says Al Mahaijri|
|Carbery sends Munster through and ends Exeter´s lingering Champions Cup hopes|
|Dyche defiant despite offside call|
|Hasenhuttl rates Everton win as Southampton´s best|
|Benitez looking up the table after Schar inspires win over Cardiff|
|RB Leipzig 0 Borussia Dortmund 1: Witsel restores six-point cushion|
|Swansea City 1 Sheffield United 0: McBurnie punishes wasteful Blades|
|Cardiff sign Sala from Nantes for club-record fee|
|Arsenal 2 Chelsea 0: Lacazette and Koscielny fire Gunners to rousing derby win|
|Huesca 0 Atletico Madrid 3: Dominant Atleti keep pressure on Barca|
|Rashford arguably league´s best striker with Kane out - Solskjaer|
|Hafeez plays steady hand as Pakistan punish Proteas´ patient approach|