The former Burnley man should get the nod ahead of Kyle Walker and will need to improve upon his Tottenham Hotspur debut against Qarabag last week.
He struggled against their pacey wingers and conceded a penalty within the first five minutes, while his much-lauded attacking threat was curtailed for the most part.
Walker has made a strong start to the season and Trippier will need to impress if he is to mount a serious challenge for a first team spot.
The Belgian started the season on the right flank for Mauricio Pochettino’s team and was one of the better performers before an untimely injury against Everton sidelined him.
Taking into account the improvement shown by Erik Lamela and the introduction of Heung-Min Son and Clinton N’Jie since then, Dembele’s task of breaking into the first-team has become a tougher one.
He is one of Spurs’ most gifted players but, as ever, the problem of finding his best position is still an issue and Wednesday’s derby clash will be a chance for him to stake a claim.
The England international has been unlucky with injuries this term but made his first appearance of the season in an impressive cameo against Sunderland last week.
He failed to build on that when given a start against Qarabag, and subsequently found himself out of the team again for Sunday’s win over Crystal Palace.
Wednesday’s game should see him brought back into the fold, and there will be no better occasion in which to kick-start his season than against the club’s most bitter rivals.