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It was Timbers who scored first on thirteen minutes just after Fernando Guerrero (who the club are still insisting on calling trialist despite leaking his details in Ventura) had hit a shot over.
But five minutes from half time Robbie Blake found the head of captain Steven Caldwell from a free kick and the skipper headed home the equaliser.
Owen Coyle made substitutions on the hour and six minutes later Kevin McDonald set Richard Eckersley free down the right and his first time cross was hit home by Steven Thompson who had just come on and netted with his first touch.
The hosts equalised with eight minutes to go and then with three minutes remaining were reduced to ten men when Knowles brought down Guerrero and decided to have a word with the referee.
Burnley suffered a blow right on time when Michael Duff sustained an ankle injury in the baseball pitching area and when the final whistle blew it too us to extra time.
Three days after Chelsea, on Sky's Soccer AM, Caldwell said had he not been sent off he would have taken the first penalty. He did this time but failed to score as did Portland with their first.
Chris Eagles and Joey Gudjonsson both scored whilst they responded with successful penalties. That was 2-2 after three each and then Kevin McDonald scored only for Brian Jensen to save their fourth.
That left the familiar situation of Wade Elliott stepping up to take the last one and give Burnley victory. This time he made no mistake and the Clarets won the shoot out 4-2.
The teams were;
Portland Timbers: Cronin, Knowles, Higgins, Nishimura, Danso, Farba, McManus, Savage, Pore, McLaughlin, Josten. Subs: Visser, Dunn, Keel, Thompson, Polti, Cameron, Nimo, Lopez, Keita, Forrest.
Burnley: Brian Jensen, Tyrone Mears (Richard Eckersley 60), Clarke Carlisle (Michael Duff 60, David Edgar 90), Steven Caldwell, Christian Kalvenes (Stephen Jordan 60), Graham Alexander (Joey Gudjonsson 60), Fernando Guerrero, Wade Elliott, Chris McCann (Kevin McDonald 60), Robbie Blake (Chris Eagles 60), Steven Fletcher (Steven Thompson 66). Subs not used: Diego Penny, Brian Easton, Remco van der Schaaf.
Attendance: 9,078.