Born in
Buenos Aires, Angelillo started playing professionally in
Arsenal de Llavallol in 1952. In 1955 he played with
Racing Club de Avellaneda and moved to
Boca Juniors in 1956. Angelillo was part of the
Argentina national team that won the
1957 South American Championship. That team, and its forward line in particular, was nicknamed
The Angels with Dirty Faces (a reference to the then-celebrated
Angels with Dirty Faces movie) due to both their irreverent style of play as well as to their less than rigorous attitude to training. The nickname followed Angelillo when he, along with fellow national team forwards
Omar Sívori and
Humberto Maschio, moved from Argentina to play football in
Italy after the tournament. There, the trio was also known as
The Trio of Death due to their clinical ability in scoring goals. In 1957 Angelillo was signed by the Italian club
Internazionale by the club's president at the time,
Angelo Moratti; he made his Serie A debut with the club on 8 September 1957, in a 0–0 home draw against
Torino, and scored 16 goals in his
first season. From 1957 to 1961, he played 127 games with the
Nerazzurri, scoring 77 times. In Serie A, he appeared in 113 matches and scored 68 goals for Internazionale, also serving as the club's
captain. During the
1958–59 Serie A season, Angelillo scored 33 goals in 33 matches, finishing the season as the
tournament's top scorer. His goal total was the highest since
Gunnar Nordahl had scored 34 in the
1950–51 Serie A season, and is still the record for most goals in a single 18-team Italian division season; Although Angelillo was Internazionale's highest goalscorer while he was playing there, he did not win any titles with the
Nerazzurri. When the club appointed
Helenio Herrera as the team's new manager, Angelillo's independent nature, rebellious character, and hedonistic lifestyle off the pitch led to several disagreements between the two; as a result, Angelillo was sold to
Roma during the
1961–62 season, for 270 million lire, in spite of offers in Argentina from his former club, Boca Juniors. From 1961 to 1965, Angelillo played 106 games with Roma in Serie A, scoring 27 times, winning the
1960–61 Inter-Cities Fairs Cup, and the 1963–64
Coppa Italia with the club. He then spent
one season at
Milan, scoring one goal in 11 matches. The following year, he signed with
Lecco, playing 12 matches and scoring one goal, with the team being relegated to
Serie B at the end of the season. Wanting to return to first division football, he subsequently had a trial with
Napoli, before agreeing to return to Milan as a reserve; he only made three appearances, scoring one goal, winning the
1967–68 Serie A title with the club, although he did not appear in Milan's victorious
1967–68 European Cup Winners' Cup campaign that season. In order to gain playing time he then moved to
Genoa in Serie B, where he made 22 appearances, scoring five goals. His next and last team was Angelana, which he joined in 1969 as a player-manager, before retiring from professional football in 1971. ==International career==