Torquay 0 Pompey 0 (Pompey win 5-3 on penalties)
Pompey showed nerves of steel to beat Torquay on penalties and progress into the second round of the Johnstone’s Paint Trophy.
The Blues had enjoyed the lion’s share of possession during the 90 minutes, but were unable to create many clear-cut chances.
They showcased some fine finishing from the spot, however, and Yassin Moutaouakil’s outrageous effort won it for the Blues after Lee Mansell had blazed over.
Guy Whittingham made two changes from the side that lost to Chesterfield in the league on Saturday.
Ryan Bird made his first Pompey start up front, while Jed Wallace returned wide on the right.
Patrick Agyemang did not make the trip to Devon, while David Connolly served the first match of a three-game suspension.
The tie did not get off to a blistering start, although Andy Barcham’s curling shot was held by Gulls keeper Martin Rice following one of the winger’s trademark mazy runs.
Torquay had a couple of half-chances either side of that, with Ben Harding sending a free-kick straight into the wall and Damon Lathrope volleying high over the crossbar.
Holmes – playing just behind lone striker Bird – sent a dangerous ball into the box on 16 minutes, but Sonny Bradley’s header was straight at Rice.
Wallace then saw his shot blocked in a crowded area after a Holmes corner had been headed back across goal.
Pompey were totally dominating possession, but the game was struggling with a lack of quality from both sides.
It took until 37 minutes until the Blues next created a decent opening, with Barcham’s looping effort deflected narrowly over.
Wallace then sent a fine pass into the Torquay pass from deep, but Bird took a heavy first touch and the chance disappeared.
Half Time: Torquay 0 Pompey 0
The second half began in the same fashion as the first had ended – with Pompey enjoying plenty of the ball, but doing little with it.
Set-pieces were proving to be their main threat, but Bird was unable to guide his header on target after meeting Holmes’ corner on 61 minutes.
Wallace then tried to surge through the middle and made good progress before eventually being crowded out in the box.
Whittingham made a change on 68 minutes, bringing on Tom Craddock to replace Bird up front.
And moments later Romain Padovani came on in midfield, with skipper Johnny Ertl making way.
Chances were still proving hard to come by, although Holmes did see his angled drive deflected behind off Aaron Downes.
From the resulting corner Holmes cut the ball back into a penalty area teeming with maroon and salmon pink shirts, but unfortunately his pass failed to pick out any of them.
Pompey had suddenly found some impetus and Barcham rounded Rice, only to see his cross cleared off the line.
The Torquay keeper then made a superb save, pushing over Bradley’s thumping close-range header after the centre-back had met Wallace’s pin-point cross.
But the hosts also stepped up a gear and John Sullivan had to fling himself to his right to keep out a rasping effort from his namesake, Gulls substitute Daniel Sullivan.
Craddock also went close at the other end, showing neat control to bring down Danny East’s long ball before drawing a save from Rice.
But the Blues were unable to break the deadlock, sending the tie into a penalty shoot-out.
Full Time: Torquay 0 Pompey 0
Bradley stepped up first for Pompey and coolly sent Rice the wrong way, before Karl Hawley levelled by firing the ball straight down the middle.
Wallace was next up and confidently found the bottom corner, but Callum Ball then did exactly the same for the hosts and Holmes also found the same bottom-left corner for the third spot-kick in a row.
Mansell was brought on especially for the shoot-out seconds before the final whistle, but blazed high over the bar.
Craddock kept this calm to, once again, find the bottom corner, while Dale Tonge kept Torquay in it with a thumping finish.
Moutaouakil then audaciously chipped the ball straight down the middle to send Pompey into the second round.
Torquay (4-4-2): Rice; Tonge, Pearce, Downes (c), Cruise; Chappell (Sullivan 59), Lathrope (Mansell 90+2), Harding, Cameron (Hawley 90+2); Ball, Benyon
Subs not used: Thompson, Nicholson
Pompey (4-4-1-1): Sullivan; Moutaouakil, Devera, Bradley, East; Wallace, Ertl (c) (Padovani 71), Ferry, Barcham; Holmes; Bird (Craddock 68)
Subs not used: Smith, N’Gala, Butler
Referee: Keith Hill
Attendance: 1,951 (372 Pompey fans)