The duo played out the League Cup final in 2008, with a Jonathan Woodgate header settling the tie in extra-time and handing Spurs a famous victory.
This time around, however, Premier League leaders Chelsea are in far better shape to take on their London rivals and Redknapp is backing Blues boss Jose Mourinho to end his personal trophy drought.
“This is a hard game to call, given the extreme results we’ve seen in the past two fixtures between the sides, but I can’t help feeling that tiredness will tell for Spurs,” Redknapp told Sky Sports.
“I’m predicting a draw in 90 minutes, but Chelsea to lift trophy. That would make it 10 wins in 12 major finals for Mourinho - an incredible record - and give him significant revenge for that shock on New Year’s Day. “
Are Spurs disadvantaged going into Sunday’s final?
There isn’t much doubting that the Blues are favourites heading into Sunday’s encounter at Wembley, but too much has been made of Spurs’ Europa League defeat.
Mauricio Pochettino was always likely to rest players and while progression to the last-16 would have been widely embraced in North London, it wasn’t a necessity and certainly not a primary target.
The League Cup, a domestic trophy and a chance to win at Wembley, is, on the other hand, a much bigger deal and Spurs’ starting XI on Thursday night in Italy reflected that.
Their squad might be slightly weary, but adrenalin and excitement will soon overcome any tiredness and their 5-3 victory over Mourinho’s side at White Hart Lane will psychologically help the Lilywhites.
It’s an incredible occasion, and observers who intend on tuning in to watch it will be treated to an intriguing encounter between two excellent teams who will give their all in pursuit of victory.