The Cherries were knocked of the Johnstone's Paint Trophy by Portsmouth after a penalty shoot-out.
Luke Rodgers, Ashley Harris, Liam Walker and Brian Howard made no mistake 12 yards but substitute Marc Pugh missed the decisive strike in front of the travelling contingent.
Shaun MacDonald had scored either side of Rodgers’ equaliser, before Howard sent the game to spot kicks with a spectacular strike midway through the second half.
The Cherries looked the most likely side to progress through to the second round in a frantic final 20 minutes at Fratton Park, but were unable to find a way past Pompey ‘keeper Mikkel Andersen.
Paul Groves made five changes to his starting line-up, handing starts to Wes Fogden, Richard Hughes and Josh McQuoid starts after they appeared from the bench in the defeat to Sheffield United on Saturday.
MacDonald got the Cherries off to a dream start when he nodded Simon Francis’ cross beyond the outstretched Mikkel Andersen after just four minutes.
Andersen got a fingertip to the header but couldn’t prevent MacDonald opening his account for the season.
Moments later, Steve Cook burst forward from left back and sent a powerful long range effort just wide after skipping away from his marker as the Cherries made an impressive start to the contest.
MacDonald and Francis almost combined again to extend the lead as the full-back picked out the Welshman with another pin point cross, but he was unable to force his header goalwards.
But it wasn’t all one way traffic, and Shwan Jalal had to be alert to beat away Howard’s drive from 25 yards.
Michael Apleton’s side began to enjoy some possession with half an hour gone, and Rodgers was unlucky to see his shot roll wide after twisting and turning away from a couple of defenders on the edge of the box.
The Cherries made a strong finish to the end to the first half, and McQuoid played in Fogden with an incisive through the ball to send the tireless midfielder one on one with Andersen in front of the Fratton End.
The former Havant & Waterlooville man appeared to be in two minds whether to go for goal or set-up Grabban for a simple tap-in, and sidefooted past the Pompey ‘keeper’s right hand post.
Just as the visitors had seemed to have taken control of the game, Rodger’s nipped in front of Tommy Elphick to guide Mustapha Dumbuya’s low cross into the net just on the stroke of half-time.
Both Fogden and McQuoid went close to putting the Cherries back in front early in the second period. First, Fogden saw his low shot saved well by Andersen before McQuoid narrowly missed out on converting Grabban’s cross.
But their pressure paid dividends as MacDonald smashed the ball into the back of the net from 20 yards after he was teed up Richard Hughes.
It took an unbelievable goal-line clearance from Kevin Long to stop Fogden capitalising on the Cherries dominance and heading into an empty net, as he followed up Grabban’s shot.
But they were made to pay for allowing Howard too much space less than a minute after Fogden been denied by the post.
The Pompey captain picked his spot from 25 yards out to round off a swift counter attack and put the hosts back on level terms.
The leveller sparked the game into life and both teams had chance to win the tie in a frantic final 20 minutes.
MacDonald looked like he had done all the hard work after bringing down Richard Hughes’ raking pass with a sublime touch before putting his shot wide.
Substitute Lee Barnard was set to silence the home fans once again, as he had done on the opening day of the season as he collected a loose ball inside the area, only to have his goalbound effort deflected behind for a corner.
Marc Pugh was sent on as Groves’ second replacement as they looked for a late winner but it would take penalties to separate the two teams after a compelling 90 minutes.
Cherries: Jalal, Francis, Elphick, Addison, Cook, Fogden (Pugh, 85), Arter, MacDonald, Hughes (Partington, 88), McQuoid (Barnard, 68), Grabban.
Substitutes: Flahavan, Zubar.
Goal: MacDonald (5 & 59)
Booked: Fogden, Hughes.
Portsmouth: Andersen, Dumbuya, Long, Thompson (Williamson h/t), Harley, Harris, Howard, Connolly (Clifford, 76), Russell, McLeod (Walker, 63), Rodgers.
Substitutes: Eastwood, Webster.
Goal: Rodgers (45), Howard (67)
Booked: Long, Howard.
Attendance: 5, 979.