The Spurs boss faces the man who once reigned supreme at White Hart Lane on Sunday.
The Queens Park Rangers boss enjoyed three seasons of thrilling football in north London, finishing fourth, fifth and fourth again with Spurs - and also reaching the quarter-finals of the Champions League.
And, despite the manner of his exit from White Hart Lane, a popular view seems to be that few can compare to the footballing success Redknapp enjoyed at Tottenham.
A view expressed frequently in the comments of this very website suggests the only reason the 67-year-old left the club was that he took his eye off the ball when he was touted for the England job.
That aside, though, the highs he achieved at Spurs will be difficult to surpass in the coming seasons.
Can Pochettino do it?
He's certainly made a good - if not spectacular start - winning both of his opening competitive games in north London. His playing style should reap similar rewards to Redknapp's, meanwhile, as he favours an attacking, high-pressing game.
Indeed, it seems a common perception is that, if anyone can match the current QPR boss's achievements at Tottenham, it is Pochettino.
But times are tough for the north London side. The top four look strong and Everton are also in contention for a spot, at least, within the top five. And, if the sleeping giant that is Manchester United awakens, Spurs will have even more competition.
Former Southampton boss Pochettino, then, will have to take things steadily, for instant success looks highly unlikely.
Will he be able to match the heights of the Redknapp era? Maybe with time. But, as recent history shows, time isn't exactly something Daniel Levy allows for.
Can Pochettino outshine Redknapp?