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.
|Djokovic back to brilliant best as Isner is beaten|
|Celta Vigo replace Mohamed with Cardoso after Real Madrid defeat|
|Joshua intrigued by Usyk, says Hearn|
|Ibrahimovic beats Rooney to MLS Newcomer award|
|Rams WR Kupp out for season with torn ACL|
|Sturridge denies ever gambling on football following FA charge|
|Koeman understands De Ligt´s Eredivisie frustrations|
|Jimmy Butler trade: 76ers acquire Timberwolves star in blockbuster deal|
|´Improve your attitude´ - Deschamps issues Dembele warning|
|Sturridge charged with misconduct over alleged breach of betting rules|
|Saints sign Marshall following Bryant injury|
|Mendy suffers knee injury, leaves France squad with Lacazette|
|Zverev beats Cilic in error-strewn London battle|
|Rafinha replaces injured Casemiro in Brazil squad|
|´One-dimensional´ Australia batsmen need work before World Cup - Finch|
|Mancini keen to work with ´incredibly gifted´ Tonali|
|Italian manager of the year Allegri targets long Juve stay|
|Injured Lee departs as Wales prepare squad for Tonga|
|Conte content to wait until June for coaching return|
|Etzebeth set to return, Whiteley a doubt for Scotland Test|
|In-form Verstappen does not need distractions from 2019 challenge|
|FA asks Guardiola to explain Manchester derby referee comments|
|LaLiga MVP Messi hopes the division stays wide open|
|Murray and Henshaw out of All Blacks Test|
|Injured Man Utd duo Pogba and Martial drop out of France squad|
|Modric cannot always be the best - Dalic|
|Very troubling times - LeBron James alarmed by gun violence|
|Bayern confirm Ribery ´altercation´ with reporter|
|Madrid hit by injuries to Nacho and Casemiro|
|Record-breaking Mushfiqur torments Zimbabwe|
|Spartak Moscow appoint Oleg Kononov|
|Rooney predicts ´exciting time´ after being named in MLS Best XI|
|Former England call-up Graham replaces Thomson in Scotland squad|
|Slater and Thurston among Queensland greats to join Maroons staff|
|Rapana set for six months out after shoulder surgery|
|Alves determined to play in the Premier League|
|Rockets GM denies Anthony will be waived|
|Monaco´s plight not Henry´s fault - Silva|
|It´s like the FBI came - River assistant unable to talk to Gallardo during final|
|Norman says Washington home crowds ´just don´t really care´|
|Bucks beat Nuggets to finish gruelling schedule stretch|
|Madrid ´very happy´ with Solari, says Butragueno|
|Titans stun Patriots, Browns upset Falcons|
|Browns´ Chubb relishes record-breaking performance: It definitely is very special|
|MLS Review: Red Bulls, Atlanta to meet in conference finals|
|Neymar wants more from perfect PSG|
|Higuain is feeling a lot of pressure – Gattuso|
|I didn´t insult anyone, says apologetic Higuain|
|Allegri delighted with Juventus response|
|Kyle Busch wins at Phoenix as Harvick, Truex qualify for Championship 4|
|WATCH: Highlights of thrilling Boca-River Copa Libertadores final|
|PSG coach Tuchel demands more despite Monaco thrashing|
|Boca missed too many chances, rues Schelotto|
|Solari remains tight-lipped on Real Madrid future|
|Hamilton not surprised by Verstappen-Ocon collision|
|Ronaldo fires Juventus to Serie A record|
|Higuain did nothing serious - Ronaldo hopes Milan striker avoids ban|
|Solari completes perfect Real Madrid audition with fourth straight win|
|Verstappen ordered to do public service after Ocon scuffle|
|Nishikori stuns out-of-sorts Federer|
|Fitzgerald overtakes Owens in career receiving yards|
|Monaco 0 Paris Saint-Germain 4: Cavani hat-trick adds to Henry woes|
|Celta Vigo 2 Real Madrid 4: Solari leads Los Blancos to fourth straight win|
|AC Milan 0 Juventus 2: Higuain sent off in horror show|
|Brees leapfrogs Favre on all-time list for touchdown passes|
|Kuchar holds on to seal first title since 2014|
|Nuno proud of Wolves display at Arsenal|
|Jones fastest in NFL to reach 10,000 receiving yards|
|WATCH: Verstappen shoves Ocon after Brazilian Grand Prix collision|
|Boca Juniors 2 River Plate 2: Izquierdoz own goal ensures first leg ends level|