They began at the third level of provincial football and at the end of the season, they had already qualified to play in the higher division, finishing third behind the C teams of U Saint-Gilloise and Uccle Sport.
In total, they were relegated four times in ten years to the second division (1923, 1926, 1928 and 1931), earning themselves the mockery of local rival clubs Union Saint-Gilloise and Daring de Bruxelles.
After a bad start (two wins and four defeats in six matches), Claude Leclercq was sacked and the team was then composed by a committee (including the chairman Théo Verbeeck and the former manager and goalkeeper Florimond Plasch) up to the end of the season.
At the end of this season, Anderlecht signed striker Jef Mermans from K Tubantia FC for 125,000 Belgian francs, a record fee in Belgium at that time.
With the help of their striker (38 goals in 34 matches), soon nicknamed "The Bomber", Anderlecht won their first league title in 1946–47 after having finished second in 1943–44 and third in 1945–46 (the championship was cancelled in 1945).
However, they won again the Belgian championship that season, and played once again in the European Cup the following year, losing to Manchester United (12–0 on aggregate) in the preliminary round.
In 1958, the club celebrated their 50th anniversary by inviting Barcelona and their three Hungarian star players – Sándor Kocsis, László Kubala and Zoltán Czibor – to play a friendly game on 30 August.
On 30 September 1964, the Belgium national team, coached by Raymond Goethals, fielded 11 Anderlecht players against the Netherlands after RFC Liégeois goalkeeper Guy Delhasse was substituted, to be replaced by Jean Trappeniers.
Since the arrival of Sinibaldi, the team had played in a "Brazilian" 4–2–4 formation, a departure from the W-M tactics (defense in a W-shape and attack in an M-shape; i.e., a kind of 2–3–3–2) used by former coach Bill Gormlie.
After three consecutive title wins, Sinibaldi left the club in the summer of 1966 and was replaced by Hungarian Andreas Beres, who coached the team to two league championships in the following two seasons.
Anderlecht also participated to the next and last Inter-Cities Fairs Cup, due to their second consecutive domestic league fourth place, but they lost in the third round to Vitória de Setúbal of Portugal.
That year, Anderlecht finished on top once again with a team led by players Rensenbrink, Ludo Coeck, Paul Van Himst and Attila Ladynski.
At the start of the 1978–79 season, Anderlecht won the 1978 European Super Cup against Liverpool, winning the first leg 3–1 at home, then losing 2–1 at Anfield Road.
[14] In 1981–82, Anderlecht lost the title to Standard Liège, but they achieved their best result so far in the European Cup, reaching the semi-finals after having eliminated Juventus in the second round and Red Star Belgrade in the quarter-finals.
The day before the journey to Kuopion Pallotoverit for their UEFA Cup first round match in 1982, Paul Van Himst replaced Tomislav Ivić.
The starting 11 for the home leg of the UEFA Cup final were goalkeeper Jacky Munaron; defenders Wim Hofkens, Luka Peruzović, Morten Olsen and Michel De Groote; midfielders Per Frimann, Ludo Coeck, Franky Vercauteren and Juan Lozano; and strikers Erwin Vandenbergh and Kenneth Brylle.
Anderlecht won their 20th championship title on the last matchday of the season when they easily beat Berchem Sport (who were already relegated) while joint leaders KV Mechelen lost to Club Brugge, who needed a win to qualify for the UEFA Cup.
Franky Vercauteren and Enzo Scifo were then transferred in the summer window, while Juan Lozano had been heavily injured in a game at KSV Waregem a few months earlier.
A weakened team coached by Raymond Goethals, after Georges Leekens had been sacked in February, finished only fourth in 1987–88, behind Club Brugge, Mechelen and Antwerp, but they managed to lift the Belgian Cup for the sixth time in their history after a 2–0 victory against Standard Liège, with goals by Luc Nilis and Eddie Krnčević.
At the end of the season, and in spite of winning three consecutive Belgian championships, manager Johan Boskamp was sacked and replaced by the German Herbert Neumann.
In 1996–97, Anderlecht ended fourth in the championship, their worst ranking in the last nine seasons, but they were runners-up of the Belgian Cup, losing the final to Germinal Ekeren, 4–2 after extra time.
At the end of the season, Johan Boskamp was replaced by René Vandereycken, who was sacked before the winter break due to bad results, with only 20 points on 42 in the league and a second round elimination in the UEFA Cup at the hands of Schalke 04.
With Arie Haan, Anderlecht managed to qualify in extremis for the 1998–99 UEFA Cup, finishing fourth in the championship thanks to a goal by Gaston Taument in the last game of the season, at Beveren (0–1).
In 2000–01, their most successful European campaign since reaching the UEFA Cup quarter-finals in 1996–97, Anderlecht beat Porto in the third qualifying round of the Champions League to progress to the first group stage.
However, in their last match of the 2005–06 group phase, with Anderlecht already eliminated from the competition, it was Vincent Kompany's winning goal at Real Betis ended their nightmare run.
However, they disappointingly failed to win a single game, losing two and drawing four, and were eliminated from European contention altogether with four points in fourth place.
A win against Hapoel Tel Aviv, a loss against Getafe and draws against Aalborg BK and Tottenham Hotspur proved enough to finish third in the group to go to the next round, where Anderlecht eliminated Bordeaux.
Both clubs had finished level with 77 points after the regular season, and although Anderlecht had a better goal difference (+45 for +40 to Standard), a play-off was organised to determine the Belgian champions.
Spurred on by their own youth players Leander Dendoncker and Youri Tielemans and top scorer Łukasz Teodorczyk, Anderlecht finished 1st in the regular league.
In mid-2019, Coucke pulled off a stunt of stature by bringing in Vincent Kompany as player-trainer, but the combination of the two roles did not prove ideal upon which Frank Vercauteren was recruited as head coach.