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Berti Vogts became the first Scotland manager to lose his opening four matches in charge as the team were beaten 2-0 by South Africa in Hong Kong on this day in 2002.
Scotland had also been defeated 5-0 by France, 2-1 by Nigeria and 4-1 by South Korea following the German’s appointment as successor to Craig Brown.
South Africa took the lead in the first half through Tebogo Makoena’s finish and substitute George Komentaris added a second on the counter attack late on.
Vogts, whose side went close to equalising when Kevin Kyle hit the bar, said: “I am very optimistic. In the defending part we did well and now we have a lot of alternatives for the squad list.
“But we have to look to the midfield. For the second goal, the midfielders were all going forward and there was one mistake.
“They have to learn that that is not possible. At least one must stay in position. But it was much, much better than Korea.”
The match was the first of the Reunification Cup, and three days later Scotland’s second fixture saw them beat a Hong Kong XI 4-0.
Vogts went on to oversee Scotland reaching a Euro 2004 play-off, which they lost to the Netherlands, before resigning in November 2004, just under three weeks on from a 1-1 World Cup qualifying draw against Moldova.