Leyton Orient defeated Coventry City 4-2 on penalties in their Johnstone’s Paint Trophy tie at Brisbane Road.
The hosts were the better team during the 90 minutes but were unable to convert their chances as the match ended goalless.
The tie went straight to penalties and Jamie Jones saved from Franck Moussa while John Fleck sent his effort wide. Orient converted all four spot kicks to deservedly book their place in the next round.
Orient made five changes to their side for the match. The O's recalled Romain Vincelot following his suspension while Yohann Lasimant made his first start in place of Marvin Bartley and Dean Cox.
Gary Sawyer returned to action in defence with Mathieu Baudry serving a one-match ban after his fifth booking against Oldham on Saturday.
Shaun Batt came into the attack, following his sixth goal of the season on Saturday, alongside Jayden Stockley with David Mooney and Kevin Lisbie earning a rest.
The O's created their first chance in the opening minute when Batt's long-range effort was comfortably held by Joe Murphy. Orient threatened again when Lasimant blasted the ball over the crossbar.
It was a largely uneventful first half with both sides struggling for any momentum at Brisbane Road.
The hosts should have taken the lead shortly before the break when Lloyd James floated in a free-kick but Scott Cuthbert somehow headed just over the bar.
Orient made a bright start to the second half and Moses Odubajo fired wide. The winger had another chance from a tight angle after Joe Murphy came off his line but he could not direct his effort on target.
Conor Thomas should have done better for the visitors but his long-range strike lacked power and was straight at Jones.
The hosts created another great chance when James released Odubajo but his low strike forced an excellent save from Murphy.
Orient had an opportunity to open the scoring from a corner but Odubajo blasted over the target.
Russell Slade made his first change after 65 minutes when he introduced Mooney in place of Batt.
Coventry probably should have done better through Callum Wilson but he lofted his strike over the bar.
Orient made a second change as Cox came on in place of the quiet Lasimant with just over 15 minutes remaining.
Leon Clarke was not far away after he sent his free-kick just past the post.
The hosts came so close to a breakthrough from James' free-kick but Mooney's header was well saved by Murphy.
Orient nearly opened the scoring through Sawyer's free-kick but his effort curled just past the post. The O's made their final change when Bartley came on in place of Stockley.
The O's had a late chance to snatch the win but Mooney's effort was blocked by Murphy and the visitors cleared the danger.
The match predictably ended goalless and went to penalties to decide which team would advance to the next round.
Leon Clarke netted the opening penalty in front of the visiting fans but Mooney was on target for the O’s.
Moussa’s effort was well saved by Jones before Elliot Omozusi put the hosts in front.
Jordan Clarke then scored for City but Gary Sawyer kept Orient ahead on spot kicks.
Fleck then fired his effort past the post which enabled James to convert the decisive penalty and send Orient into the next round.
Leyton Orient: Jones; Omozusi, Cuthbert, Clarke, Sawyer; Lasimant (Cox, 73), James, Vincelot, Odubajo; Batt (Mooney, 65), Stockley (Bartley, 83)
Subs not used: Larkins, Lee
Coventry City: Murphy; Adams, J Clarke, Webster, Willis (Phillips, 65); Barton (Daniels, 73), Thomas, Fleck, Moussa; L Clarke, Wilson
Subs not used: Burge, Manset, Haynes
Referee: Tim Robinson