Cape Town - Middlesbrough have announced the departures of wing-back Carlos De Pena and striker Arnel Jakupovic.
The 24-year-old De Pena, who joined Boro from Uruguayan Primera Division side Nacional in 2015, departs for Spanish Segunda side Real Oviedo on a six-month loan.
He made 10 senior appearances while mostly playing for the U-23 side.
Jakupovic, meanwhile, has signed for Italian Serie A side Empoli for an undisclosed fee.
A former FK Austria Wien II striker, the 18-year-old Austria under-19 international signed for the Teesiders' under 23 side, also in 2015 where he scored 14 goals in 20 appearances in the Premier League 2 and UEFA Youth League.
He was restricted to just two goals in eight appearances this season having suffered injuries to his hip and hamstring.