Newcastle 1 Tottenham 2 - Third Round, September 24, 2008
Roman Pavlyuchenko opened his Spurs account with a header to set his new club on the way to victory. Jamie O'Hara made the game safe before Michael Owen netted a late consolation.
Tottenham 4 Liverpool 2 - Fourth Round, November 12, 2008
A brace apiece from Pavlyuchenko and loan signing Fraizer Campbell, his first goals for Spurs, earned the Londoners a convincing win. Damien Plessis and Sami Hyypia headed in replies for the Reds.
Watford 1 Tottenham 2 - Fifth Round, December 3, 2008
Russia striker Pavlyuchenko kept up his record of scoring in every round by equalising from the penalty spot as Spurs came from behind to win. Darren Bent grabbed the winner after Tamas Priskin had given the Coca-Cola Championship side a shock lead.
Tottenham 4 Burnley 1 - Semi-final first leg, January 6, 2009
The half-time introduction of O'Hara changed the game as Spurs turned a 1-0 deficit at the break in to a convincing win. Michael Dawson, O'Hara, Pavlyuchenko and a Michael Duff own goal put Harry Redknapp's men within touching distance of Wembley after Martin Paterson had drawn first blood.
Burnley 3 Tottenham 2 (aet) - Semi-final second leg, January 21, 2009
Two goals in the final two minutes of extra-time from Pavlyuchenko and Jermain Defoe saved Spurs from an embarrassing exit, sending them through 6-4 on aggregate. Burnley won the game 3-2, goals from Robbie Blake, Chris McCann and Jay Rodriguez having forced an extra 30 minutes.