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Biancorossi and Serie B promotion (1932–1953)   

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Starting from the 1933–34 season, Monza wore red-and-white kits.

During the 1930s and 1940s Monza played in the Prima Divisione (third level), which became the Serie C in 1935.<27> In September 1932, ahead of the 1932–33 season, Monza changed their shirt colours to red and white, which they have worn ever since.<28> They became nicknamed "i biancorossi" (the white and reds) following the colour change.<28> Monza finished in first place the following season and played a round-robin tournament with three other teams for promotion to the Serie B (second level); they finished fourth and failed to move up to the second level.<29> On 23 April 1939, the club reached the Coppa Italia quarter-finals, losing 2–1 to Serie A side Genoa.<30><31> They became the first Serie C team to reach the quarter-finals of the competition.<32>

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Between 1942 and 1945, World War II interrupted football in Italy.<33> Following the war, Monza were placed in the Serie C (third level), finishing eighth in the 1945–46 season.<34> They came close to promotion the following season, finishing third in the promotion play-offs.<35> In 1947, Peppino Borghi became president of Monza.<36> Monza, who were coached by Annibale Frossi, headed into the 1950–51 Serie C with a strong transfer campaign.<37> On 4 June 1951, Monza played away to Omegna <it> in the season's second-to-last match; Carlo Colombetti <it> of Monza scored the match's only goal with a penalty kick,<38> giving Monza their first promotion into the Serie B.<39>

Monza debuted in the Serie B on 9 September 1951, drawing to Siracusa 1–1 away from home.<40> The team only avoided relegation on the last matchday with a 2–1 home win against Piombino.<41> Against most experts' pre-season expectations, Monza finished the 1952–53 Serie B in fourth position, three points behind automatic promotion in second place.<42>

Simmenthal merger and aftermath (1955–1967)

In July 1955, ahead of the 1955–56 season, Monza merged with Prima Divisione (sixth level) side G.S. Simmenthal, the football club of the Simmenthal <it> food company.<43> A.C. Monza was renamed A.C. Simmenthal-Monza, and was headed by Simmenthal owner Claudio Sada.<44> The merger helped fund subsequent transfer campaigns.<43> The match between Monza and Verona on 8 October 1955 was the first free-to-air televised match in Italy.<45> Monza's first season under the new management was positive, finishing the season in third place.<46> In the following years, until the end of their merger in 1964, Monza alternated positive seasons (fourth and fifth place in 1958 and 1961, respectively) with negative ones (16th and 15th in 1960 and 1964).<47> On 14 July 1964, Simmenthal ceased to sponsor Monza and the club reverted to its former name.<48>

Despite Monza's stable financial situation, no one was interested in purchasing the club; Sada decided to remain president for the following season.<50> While Monza barely avoided relegation in the 1964–65 season,<51> the same could not be said about the next season: following 15 years of second-tier football, Monza were relegated to the Serie C in the last matchday of the season,<52> drawing 0–0 away to Mantova on 19 June 1966.<53> After winning the 1966–67 play-off game against Como 1–0, thanks to a lone goal by Gianluigi Maggioni <it> in the 32nd minute, Monza were promoted back to the Serie B after one year.<54>

Serie A promotion attempts (1969–1979)

The 1973–74 Coppa Italia Semiprofessionisti won by Monza

Three years after their Serie B promotion, Monza came close to reaching the Serie A for the first time in the 1969–70 Serie B under coach Luigi Radice; they needed an away win against first-placed Varese to keep their promotion chances alive on the second-to-last matchday.<55> On 7 June 1970, after just two minutes of play, Monza took the lead through Roberto Caremi <it>; in the sixth minute, Giampaolo Lanzetti <it> failed to double the lead, wasting a clear chance in front of the goal.<56> Varese won 2–1, preventing Monza from gaining promotion.<56>

In mid-1972, Giovanni Cappelletti became president of the club.<57> In his first year in charge, Monza were relegated to the Serie C after losing the last match of the 1972–73 season away to Bari 3–1.<58> Despite their relegation, Monza saw success in the Coppa Italia Semiprofessionisti, reaching the finals in 1974, 1975 and 1976, winning the first two over Lecce and Sorrento, and losing the third in a repeat of the first final.<59> Five matches before the end of the 1975–76 season, Monza were promoted back to the Serie B;<60> they also won an Anglo-Italian Cup on 19 June 1976, beating Wimbledon 1–0 in the final through a Francesco Casagrande <it> goal.<61>

During the late 1970s, Monza came close to gaining promotion to the Serie A on multiple occasions.<62> The first time was as a newly promoted team in the 1976–77 season, when they lost the season's final match 2–1 against Modena through an 81st-minute own goal.<63> The following season went in a similar fashion for Monza, losing out to direct promotion in the second-to-last matchday against Pistoiese.<64><65> In the 1978–79 Serie B season Monza again missed out on promotion in the final matches, being defeated by already-relegated Lecce in the second-to-last match.<66> Monza tied with Pescara on points for third place and the two sides played a promotion tie-breaker, which Monza lost 2–0.<67> In Cappelletti's last season as president, in 1979–80, Monza failed to gain promotion to the top flight for the fourth consecutive year. Four games from the end of the season, Monza were in third place in a spot for direct promotion; decisive defeats against Cesena and Brescia meant that Monza finished in fifth place, three points from Serie A promotion.<68>

Valentino Giambelli presidency (1980–1999)

The Stadio Brianteo (2022) has hosted Monza's home games since 1988.

Valentino Giambelli became the club president in 1980,<69> succeeding Cappelletti, and the club was renamed Calcio Monza.<70> In the 1980–81 Serie B, Monza played in a championship with historical sides Milan and Lazio;<71> both of whom had been relegated from the Serie A following the 1980 Totonero scandal.<72> Monza finished in last place and were relegated to the Serie C1 (third level),<69><73> but were promoted back one season later <it>.<74><75> They remained in the Serie B for a further four seasons before being relegated in 1986.<76>

In the 1986–87 Serie C1 <it>, players such as Alessandro Costacurta, Francesco Antonioli and Pierluigi Casiraghi, who later became established names in Italian football, made their professional debuts with Monza.<62> Captained by Pierluigi Frosio, Monza gained promotion to the Serie B in the 1987–88 season <it>,<77> and also won their third Coppa Italia Serie C, beating Palermo 2–1 at home following a goalless draw away.<79> The second leg, which was played on 11 June 1988, was Monza's last game in the Stadio Gino Alfonso Sada, after which the team moved to the newly constructed Stadio Brianteo.<80> The first match was played at the new stadium on 28 August 1988, when over 10,000 spectators attended Monza's Coppa Italia game against Serie A club Roma; against expectations, Monza won 2–1 with goals by Casiraghi and Carmelo Mancuso.<81>

After having closely avoided relegation in 1988–89 on goal difference,<82> Monza lost the 1989–90 Serie B relegation play-off against Messina on 7 June 1990, and were relegated to the Serie C1.<83><84> On 13 June 1991, Monza won a record fourth Coppa Italia Serie C, beating Palermo in the final.<85><86> They gained promotion to the Serie B in the 1991–92 season <it><87><88> but two years later, Monza finished the 1993–94 season in last place and returned to the third tier.<89>

In March 1997, Giambelli signed a collaboration agreement with Milan and Monza became a satellite team of the Rossoneri,<90> the first of its kind in Italy.<91> In June 1997, Monza returned to the Serie B after defeating Carpi 3–2 in the promotion play-off final; they were coached by Luigi Radice, who had also helped them to promotion 30 years prior.<92> The following season, newly promoted Monza changed most of their roster, introducing young players, many of whom came from Milan's youth sector.<93> The team closed the season having been on the verge of relegation.<94>