Gretna were due to play in the First Division after being relegated from the SPL. However, on 29 May 2008, they were demoted to the Third Division due to their failure to guarantee that they would fulfill their fixtures.[3] Gretna resigned from the SFL on 3 June 2008[4] with the club's administrators warning of the threat of liquidation, creating an opening in the Third Division for a new SFL member.[5] Following Gretna's demise a new club, Gretna 2008 was formed, they were given a place in the East of Scotland League, filling the gap left by Annan Athletic.[6]
Ross County competed in the First Division after being promoted as Second Division champions. Airdrie United were also promoted into the First Division, filling Gretna's space, as they were the losing play-off finalists.[3]
Stirling Albion competed in the Second Division after being relegated from the First Division as the bottom team.[7]
East Fife[8] and Arbroath[9] competed in the Second Division after being promoted as Third Division champions and Second Division play-off winners, respectively. Stranraer were also promoted into the Second Division, filling the empty space following Gretna's relegation, as they were the losing play-off finalists.[3]
Berwick Rangers[10] and Cowdenbeath[11] competed in the Third Division after being relegated from the Second Division as the bottom team and through the Second Division play-offs, respectively.
Annan Athletic competed in the Third Division after being admitted to the SFL.[12] They replaced Gretna, who resigned their league status on 3 June.[4]
13 November – A consortium led by Berwick Rangers Supporters Club agreed a deal to take over the club. Following a poor run of form, manager Allan McGonigal resigned at the same time saying "I made up my mind that when the current directors left I would move on."[20]
4 December – Scotland fail in their attempt to have the match against Norway moved to October 2009, the match was to go ahead on 12 August 2009.[22]
13 December – Celtic drew 1–1 with Heart of Midlothian at Celtic Park[23] which was followed by a reported dressing-room argument between Celtic manager Gordon Strachan and player Aiden McGeady.[24][25] This led to Strachan banning the player without pay for two weeks, after initially saying he would contest the sanction McGeady accepted the punishment[26] and later returned to the team.[27]
28 January – Shares in Berwick Rangers were transferred to complete the deal which handed control to a consortium led by Berwick Rangers Supporters Trust.[29]
31 January – St Mirren drew 1–1 with Kilmarnock in their first match at their new stadium.[30]
Source: Scottish Professional Football League Rules for classification: 1) Points; 2) Goal difference; 3) Goals scored (C) Champions; (R) Relegated Notes:
^Teams played each other three times (33 matches), before the league split into two groups (the top six and the bottom six) for the last five matches.
^Scotland were awarded an additional Europa League place as the association finished in third place of the UEFA Fair Play ranking. Motherwell earned this place as winners of the Scottish Fair Play ranking.
Source: BBC Sport Rules for classification: 1) points; 2) goal difference; 3) number of goals scored. (C) Champions; (P) Promoted; (R) Relegated Notes:
^Demoted to 3rd Division for Financial Irregularities
^Spared Relegation as Losing Finalist in the playoff due to Livingston
^The 9th placed team will be entered into a play-off with the Second Division's 2nd, 3rd and 4th placed teams. The winning team will be awarded a place in the 2009–10 First Division.
Source: BBC Sport Rules for classification: 1) points; 2) goal difference; 3) number of goals scored. (C) Champions; (P) Promoted; (R) Relegated Notes:
^The 2nd, 3rd and 4th placed teams will be entered into a play-off with the First Division's 9th placed team. The winning team will be awarded a place in the 2009–10 First Division
^The 9th placed team will be entered into a play-off with the Third Division's 2nd, 3rd and 4th placed teams. The winning team will be awarded a place in the 2009–10 Second Division.
Source: BBC Sport Rules for classification: 1) points; 2) goal difference; 3) number of goals scored. (C) Champions; (O) Play-off winners; (P) Promoted Notes:
^Cowdenbeath were promoted due to Livingston's demotion from the First Division to the Third.
^The 2nd, 3rd and 4th placed teams will be entered into a play-off with the Second Division's 9th placed team. The winning team will be awarded a place in the 2009–10 Second Division.
Scotland began the season with a friendly against Northern Ireland. Northern Ireland were denied a victory by substitute goalkeeper Allan McGregor who saved a David Healy penalty after he brought down Warren Feeney inside the area. The draw meant that Scotland had yet to win under George Burley after three matches. The 2010 World Cup qualification campaign began against Macedonia. Scotland faced an early free-kick after Macedonia striker Goran Maznov fell theatrically on the edge of the penalty area as he was challenged by stand-in captain Stephen McManus. Craig Gordon was able to tip the resulting shot onto the post, but Ilčo Naumoski followed up to score five minutes into George Burley's first competitive match. Both teams had opportunities and Scotland were denied what appeared to be a clear penalty after James McFadden was brought down but the referee waved away the appeals and booked the striker for his protests. Scotland recovered from their opening defeat with a 2–1 victory away to Iceland in what was Burley's first win as manager. Kirk Broadfoot scored on his debut and James McFadden scored from a penalty, Iceland got back into the match after captain McManus handled in the box and Eiður Guðjohnsen scored from the resulting penalty. Scotland held out for the win despite having to play the last 13 minutes down to ten men.
Scotland drew 0–0 at home to Norway despite debutant striker Chris Iwelumo being presented with an open goal opportunity from just three yards, with the ball being crossed by Gary Naysmith from the left to the right side of the goal where Iwelumo is standing, he connects with the ball but somehow manages to put the ball wide of the left post. The draw left Scotland top of Group Nine but with just four points from three games, with the Netherlands having played just one. They next played a friendly against Argentina in Diego Maradona's first match as Argentina manager, Maxi Rodríguez scored the winning goal for the Argentines in a 1–0 win.
The Netherlands beat Scotland comfortably with goals from Klaas-Jan Huntelaar, Robin van Persie and Dirk Kuyt, depleted by injuries Burley was forced to field an inexperienced side Ross McCormack making his debut started along with Christophe Berra and Allan McGregor, who were making their first competitive starts. Scotland were denied a chance to get back into the match at 2–0 down when referee Massimo Busacca (who was suspended by his home federation) disallowed a seemingly perfectly good Gary Caldwell goal, minutes later the Netherlands were awarded a penalty from which Kuyt scored. Ross McCormack and Steven Fletcher both scored their first international goals in a 2–1 win over Iceland, McCormack opened the scoring after 39 minutes firing high into the net from an Alan Hutton cross, Indridi Sigurdsson levelled for the visitors after Pálmi Rafn Pálmason hit the post, Scotland though regrouped and after 65 minutes were awarded a debatable corner which McCormack took, the ball was headed into the danger area by McManus and Fletcher headed into the net. Scotland had gained seven points from five matches and occupied second spot in Group nine, three points clear of Iceland, four matches between the other teams and Scotland retained second position having played less matches than all other teams in the group meaning they were in prime position for second place with Holland already guaranteed first, However, only the second placed teams from eight of the nine qualifying groups would go into the play-offs.