Spoilers for The Avengers: Endgame below.
When asked if Captain America would have met the Red Skull in Vormir, the shadowy realm where both Gamora and Black Widow lost their lives in pursuit of the Soul Stone in Avengers: Endgame, directors the Russo brothers unequivocally said yes.
““He would have certainly met Red Skull to return the stone,” Joe Russo said. “Unfortunately, there’s a no return policy in respect to getting Black Widow back.”
The Russo’s confirmed that, at least according to their artistic interpretation of Avengers: Endgame, Captain America lives out his life with Peggy Carter in an alternate universe.
Source: IGN.com Russo's Say Captain America 'Certainly' Met Red Skull In Endgame