Portsmouth F.C . won the FA Cup twice and the FA Charity Shield once .
Portsmouth have also won the FA Cup twice in 1939 and 2008 , the FA Charity Shield once in 1949 and the EFL Trophy once in 2019.  have also won the second tier division title once in 2002–03 , the third tier division title three times in 1923–24 ( South ) , 1961–62 , 1982–83 and the fourth tier division title once in 2016–17 .