George Burley's first competitive game in charge of Scotland ended in defeat as Macedonia secured a 1-0 triumph in the 2010 World Cup qualifier at the Skopje City Stadium.
Ilco Naumoski struck the only goal of the encounter on five minutes as the Scots struggled in the heat and against their opposition in the first period.
Macedonia's crucial strike came after goalkeeper Craig Gordon parried Goce Sedloski's free-kick onto the post with Naumoski pouncing from close range.
Scotland improved in the second half but were unable to find a leveller while they had to rely on Gordon to make excellent saves from Goran Maznov to leave Burley with much to ponder ahead their next fixture in Iceland on Wednesday.
Burley had his preferred team in mind for several weeks ahead of the match and there were no real surprises when his starting XI was revealed.
Kenny Miller and James McFadden both started and were given the task of providing an attacking threat despite a less than inspiring partnership in last month's drab goalless friendly against Northern Ireland at Hampden.
With West Brom's James Morrison injured, Barry Robson was given the nod in midfield alongside Celtic team-mates Paul Hartley and Scott Brown, as well as Darren Fletcher.
As expected, stand-in skipper Stephen McManus was able to shake off a knock he picked up in last week's Old Firm derby to take his place in the heart of defence with Gary Caldwell.
The 1,000 travelling supporters witnessed the worst possible start when Scotland found themselves trailing with just five minutes on the clock.
The Macedonians earned a free-kick just outside the area when McManus was deemed to have fouled Goran Maznov and Sedloski stepped up for the set-piece. His effort was touched on to the post by goalkeeper Craig Gordon but Naumoski pounced to rifle home the rebound from six yards.
The Scots could have hit back through a free-kick of their own when Graham Alexander was fouled by Robert Petrov but Robson's curling shot was weak and easily smothered by goalkeeper Petar Milosevski.
Macedonia threatened again when Petrov provided a cross from the left for Goran Pandev but his ferocious volley cannoned off the body of Caldwell, denying the home side's star man the chance to add to their tally.
Scotland then had a decent chance of their own when Fletcher set up McFadden and he embarked on a run which took him past several red jerseys only for his shot to be blocked by the body of Igor Mitreski, before the Birmingham striker nodded the rebound wide.
At the other end, the home fans screamed for a penalty when Maznov went to ground under pressure from Gordon but the Macedonia man appeared to make the most of it and the pleas were ignored by referee Pavel Kralovec.
Veliche Shumolikoski then released Maznov on a surging run which was halted by Caldwell. The ball broke to Pandev but he fired straight at Gordon in what proved to be the last real chance of the first half.
Scotland tried to force their way back into the game after the break and Scott Brown drew a decent save from Milosevski with a well-struck shot from distance, before the heroics of Gordon prevented the visitors from falling further behind.
A Pandev corner was cleared as far as Shumolikoski who unleashed a thunderous long range effort that the Scots keeper just managed to tip over the crossbar with one hand.
Gordon then punched to safety a dangerous cross into the box from Pandev before Maznov could connect with a header at his right post.
Scotland made their first change when Kris Commons replaced Hartley, before Gordon was again called into action to block a point-blank effort from Naumoski.
Burley's men failed with their own claim for a penalty when Miller played through McFadden and he went to ground as the goalkeeper dived to claim the ball.
No spot-kick was forthcoming and all McFadden earned for his protests was a yellow card from the Czech official.
Miller was withdrawn for Rangers team-mate Kris Boyd with ten minutes to go as the Scots had one last throw of the dice but Macedonia held on for maximum points with Burley still seeking his first win as Scotland manager.
| Macedonia | Team Statistics | Scotland |
| 1 | Goals | 0 |
| 1 | 1st Half Goals | 0 |
| 5 | Shots on Target | 6 |
| 3 | Shots off Target | 3 |
| 6 | Blocked Shots | 3 |
| 4 | Corners | 7 |
| 16 | Fouls | 11 |
| 1 | Offsides | 2 |
| 3 | Yellow Cards | 1 |
| 0 | Red Cards | 0 |
| 76.1 | Passing Success | 81.1 |
| 33 | Tackles | 18 |
| 78.8 | Tackles Success | 77.8 |
| 46.3 | Possession | 53.7 |
| 44 | Territorial Advantage | 56 |

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| Saturday 21st November | |
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| 12:45 | Liverpool vs Man City |
| 15:00 | Birmingham vs Fulham |
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| Sunday 22nd November | |
| Barclays Premier League | |
| 13:30 | Bolton vs Blackburn |
| 15:00 | Tottenham vs Wigan |
| 16:00 | Stoke vs Portsmouth |
| Wednesday 25th November | |
| Barclays Premier League | |
| 19:45 | Hull vs Everton |
| 20:00 | Fulham vs Blackburn |
| Saturday 28th November | |
| Barclays Premier League | |
| 15:00 | Blackburn vs Stoke |
| 15:00 | Fulham vs Bolton |
| 15:00 | Man City vs Hull |
| 15:00 | Portsmouth vs Man Utd |
| 15:00 | West Ham vs Burnley |
| 15:00 | Wigan vs Sunderland |
| 17:30 | Aston Villa vs Tottenham |
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|---|---|
| Sunday 8th November | |
| Barclays Premier League | |
| Chelsea 1 - 0 Man Utd | |
| West Ham 1 - 2 Everton | |
| Wigan 1 - 1 Fulham | |
| Hull 2 - 1 Stoke | |
| Saturday 7th November | |
| Barclays Premier League | |
| Wolverhampton 1 - 4 Arsenal | |
| Man City 3 - 3 Burnley | |
| Tottenham 2 - 0 Sunderland | |
| Blackburn 3 - 1 Portsmouth | |
| Aston Villa 5 - 1 Bolton | |
| Wednesday 4th November | |
| Barclays Premier League | |
| West Ham 2 - 1 Aston Villa | |
| Sunday 1st November | |
| Barclays Premier League | |
| Birmingham 0 - 0 Man City | |
| Saturday 31st October | |
| Barclays Premier League | |
| Man Utd 2 - 0 Blackburn | |
| Sunderland 2 - 2 West Ham | |
| Portsmouth 4 - 0 Wigan | |
| Bolton 0 - 4 Chelsea | |
| Stoke 2 - 2 Wolverhampton | |
| Fulham 3 - 1 Liverpool | |
| Burnley 2 - 0 Hull | |
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