The Pompey right-back is currently on a second loan spell with Oxford City.
The National League South strugglers are booked in for a trip to Notts County on Saturday in the FA Cup second round.
However, before that tantalising occasion, Oxlade-Chamberlain will line up for Pompey’s reserves against Barnsley (7pm) in this evening’s Premier League Cup clash.
Although yet to make a first-team outing under Kenny Jackett, the 19-year-old has been a reserve-team regular.
And with a visit to Meadow Lane – the memorable scene of Pompey’s League Two promotion – on the horizon, it promises to be a busy week for the youngster.
Jackett said: ‘Christian will play for us against Barnsley – and he also has a great game coming up against Notts County.
‘He recently joined Oxford for a second spell, taking him up to January.
‘He was there earlier in the season, but we recalled him when we were struggling with a few injuries. He was an unused substitute in our first team for a few times, too.
‘Now he has gone back out on loan and I want him to continue playing at right-back, learning and improving.
‘I think in the long-term there is a player in there at right-back and playing in the National League South at the moment is a very good chance for him.
‘He has the attributes to play at full-back. He has the power of a modern-day full-back and hopefully can get up and down the line.
‘He’s 19 and, by the time he is 21, I think he’s going to be a really good size and a very good athlete. It will be interesting looking at him in that period.
‘We have lots of people back fit now, so he has gone up there to Oxford for games.’
Pompey may be out of the FA Cup, yet remain in action this weekend through the rearranged Checkatrade Trophy match against Northampton.
That has hampered their team selection for tonight’s Group F fixture in the Premier League Cup.
Those expected to play alongside Oxlade-Chamberlain in Robbie Blake’s side, though, include Drew Talbot, Adam May, Jez Bedford and Theo Widdrington.
The Blues are currently third, having taken a point from two group matches.