Lewis Stockford and Carl Walshe have joined AFC Totton and Frome Town respectively on loan.
The duo will both spend a month with the Evo-Stik Southern Premier Division sides.
Stockford is a 19-year-old midfielder who signed a professional contract last summer and played for the Blues on their pre-season trip to America.
Academy striker Walshe, also 19, joined Pompey from Irish side Home Farm in 2009.
AFC Totton currently sit second in the table – five points behind leaders Brackley with three games in hand – while Frome are 12th.
Pompey and Frome Town have a long history, with the Blues signing Billy Haines from the Robins in 1923.
The centre-forward went on to become arguably the club’s most popular player during the 1920s, scoring 128 times in 179 appearances between 1923 and 1928.