16 June: The SPL fine Livingston £15,000 for breaching transfer regulations after it emerged that amateur signing from last season, Hassan Kachloul, was paid money during his time at the club.
30 June:George Burley is confirmed as the new manager of Hearts after days of discussions with Chief Executive Phil Anderton and major shareholder Vladimir Romanov.
27 July: Celtic manager Gordon Strachan is under pressure after his first match in charge as Celtic are beaten 5–0 away to Artmedia Bratislava in the first leg of their Champions League second qualifying round match, all but ending their European hopes for the season.
2 August: Celtic crash out of Europe, despite beating Artmedia Bratislava 4–0 in the second leg of their Champions League qualifier.
7 August: Hearts demonstrate their SPL title-challenge credentials as they claim a 4–0 home victory over local rivals Hibernian.
22 October: Despite their unbeaten start to the SPL season, Hearts Manager George Burley departs from his position just hours before their league match with Dunfermline. A club statement after the game declared that the departure of Burley had been mutually agreed and that there were "irreconcilable differences" between him and the Hearts board. Throughout his short spell in charge rumours persisted about an uneasy relationship between Burley and major shareholder Vladimir Romanov with Romanov having bought players without the consent of the Manager.
13 January: Dundee United appoint Inverness Manager Craig Brewster at the helm after the sacking of Gordon Chisholm.
19 January: Wolves and Scotland striker Kenny Miller signs a pre-contract agreement to play for Celtic from next season. The former Rangers player will become only the third man to play for both Old Firm clubs since the Second World War.
27 January: Inverness coach and former player Charlie Christie is appointed as the club's new manager.
8 February: Hearts principal shareholder Vladimir Romanov agrees to a meeting requested by the Hearts players, following speculation that Romanov had selected the team in the previous two matches, Manager Graham Rix meanwhile, refused to confirm or deny the speculation.
9 February: Rangers Chairman David Murray confirms that manager Alex McLeish will leave the club at the end of the current season. He also stated that an announcement regarding a new manager and significant levels of investment into the club will be made in March.
11 February: Livingston Manager Paul Lambert resigns after defeat at home to Dunfermline left them six points adrift at the bottom of the table having taken just 12 points from 26 games.
15 February: Livingston appoint former player John Robertson as their new Manager.
8 March: Rangers Chairman David Murray's announces a 10 year licence agreement with sports retailer JJB Sports. Rangers will net an initial £18m and a minimum of £3m each year on royalty fees for the duration of the licence.
11 March: Rangers confirm that former Olympique Lyonnais manager Paul Le Guen will succeed Alex McLeish at the start of the 2006–07 season, signing a three year contract.
16 April: St. Mirren win promotion to the SPL after a 2–1 win over Dundee.
29 April: Livingston are relegated from the SPL after a 1–0 defeat to Inverness Caledonian Thistle. Meanwhile, Cowdenbeath clinch the Third Division title after beating Elgin City 2-1.
3 May: Hearts clinch second place and a spot in the Champions League qualifiers with a 1–0 home win over Aberdeen. This marks the first time since the 1994–95 season that the Old Firm clubs have failed to finish in the top two places in the SPL. Hearts' win also ensures that Gretna will play European football next season in the UEFA Cup.
13 May: Hearts win the Scottish Cup 4–2 on penalties after a 1–1 draw with Second Division champions Gretna.
The Scottish Premier League 2005–06 season finished in May 2006 with Celtic as champions. Livingston were relegated to the First Division and First Division winners St. Mirren were promoted. For the first time in 11 years, when Celtic finished fourth behind Rangers, Motherwell and Hibernian, the Old Firm were separated with Rangers finishing third behind Hearts. Kris Boyd was the top scorer with 32 goals (15 for Kilmarnock and 17 for Rangers). Attendances went up to 3.7 million, the highest figure in top-flight Scottish football since the 1960s.
Hearts became the first non-Old Firm club to win the Scottish Cup since they themselves lifted the trophy in 1998. Second Division side Gretna became the first club in history from the third-tier of Scottish football to reach the final. Celtic meanwhile lifted the League Cup in what was manager Gordon Strachan's first trophy as manager. St. Mirren were winners of the Challenge Cup in a season that would eventually see them promoted to the SPL. Auchinleck Talbot lifted the Junior Cup.
Scotland failed in their attempt to qualify for the 2006 World Cup, eventually finishing third in their group. However, significant improvement was shown in results with just two defeats from nine matches, compared with four defeats from nine during the previous season. Wins against Moldova and Norway and a draw at home to Italy had raised hopes that Scotland could gain second place behind Italy and therefore enter the play-offs. However a 1–0 defeat at home to Belarus ended their hopes of qualification. They finished the season strongly, however, with a victory over Slovenia and also lifted the Kirin Cup — beating Bulgaria and drawing with hosts Japan.