Otto Glória, José Maria Pedroto and Sérgio Conceição have won the competition on four occasions, while János Biri and Fernando Vaz guided their teams to the trophy on three occasions. Otto Glória was the first manager to have won the competition with two different clubs, a feat later achieved by Fernando Vaz, José Maria Pedroto, Jimmy Hagan and Rui Vitória.
Nine managers led their teams to consecutive wins in the tournament: János Biri (1943, 1944), Cândido de Oliveira (1946, 1948)[nb 1], Ted Smith (1949, 1951)[nb 2]Mário Lino (1973, 1974), John Mortimore (1986, 1987), Fernando Santos (2000, 2001), Paulo Bento (2007, 2008), Jesualdo Ferreira (2009, 2010) and Sérgio Conceição (2022–2024). José Maria Pedroto (1975–1977) and Sérgio Conceição (2022–2024) are the only managers to have won three consecutive times; the latter is the only to have won four times with the same club.