Barnsley lost 5-4 on penalties after a 0-0 draw at League One Bolton Wanderers in the EFL Cup first round on Tuesday evening.
Substitute Devante Cole was the only player to miss in the shoot-out on his 'second debut' for the club after a 2014 loan spell.
The Reds were on top in the first half but missed big chances then the hosts were the better team after the break.
Markus Schopp made eight changes from Saturday's draw at Cardiff City in the Championship opener, with only Michal Helik, Callum Styles and Cauley Woodrow staying in the side. There was no involvement at all for Callum Brittain, Liam Kitching, Ben Williams, Romal Palmer and Carlton Morris.
George Miller made his full debut – 922 days after signing for the club – at right wing-back, as did Josh Benson in central midfield. Herbie Kane and Devante Cole were on the bench after injuries as was teenager Jason Sraha.
Barnsley had a goal ruled ruled out in the third minute when Miller sent in an excellent cross to Victor Adeboyejo whose header was straight at the goalkeeper then Woodrow turned in from almost on the line but was flagged offside. Replays showed he was onside.
Clarke Oduor should have scored in the ninth minute when he met a left-wing Jordan Williams cross unmarked five yards out but scuffed the shot and the goalkeeper gathered.
Barnsley continued to dominate the ball but the match became more of an even contest, with Bolton's Antoni Sarcevic sending a long-range effort just wide of the top right corner.
Adeboyejo came close again on 29 minutes when he fired wide from the edge of the box on the right after Jasper Moon won the ball and Oduor played a good throughball.
Bolton could have taken the lead three minutes later with their first real chance. Sarcevic ran down the right of the Reds box, after a home corner was cleared, and passed to George Johnston whose low ten-yard shot was saved by Jack Walton diving down to his right.
Early in the second half, Ricardo Santos headed well wide from a right-wing corner by ex-Red Lloyd Isrove then another former Barnsley man Gethin Jones saw his effort from the right of the box beaten away by Walton.
Schopp brought on Cameron Thompson for his professional debut, in place of Adeboyejo, then replaced Styles and Woodrow with Kane and Cole.
Barnsley struggled to find the same rhythm in the second half but came close on 71 minutes when Cole headed a Miller cross at the goalkeeper under pressure from a defender 12 yards out.
Bolton almost won it in the 90th minute but Walton saved a Josh Sheehan shot from the edge of the box then Amadou Bakayoko headed the rebound over.
Benson, Kane, Helik and Jordan Williams all netted for Barnsley before Cole saw his effort saved by Dixon diving to his left and Bolton completed a perfect set of five spot-kicks to reach the second round.
Bolton (4-3-3): Dixon; Jones, Santos, Johnston, Gordon; MJ Williams, Lee (Sheehan 79mins), Sarcevic; Isgrove, Doyle (Kachunga 66), Delfouneso (Bakayoko 56). Unused: Sheehan, Thomason, Tutte, Brockbank, Darcy. Yellow cards: Jones.
Barnsley (3-4-3): Walton; Moon, Halme, Helik; Miller, Styles (Kane 60mins), Benson, J Williams; Oduor, Adeboyejo (Thompson 56), Woodrow (Cole 60).
Subs: Collins, Sraha, Sibbick, Frieser. Yellow cards: Benson, Kane.
  • 8:04pm
    3 Barnsley have a goal ruled out. George Miller's excellent cross is headed straight at the goalkeeper by Adeboyejo from close range and Woodrow taps in but is offside
  • 8:07pm
    Good start for the Reds. Adeboyejo really should have scored that but it was a nice move. Miller has made a really lively start
  • 8:08pm
    7 Home goalkeeper Joel Dixon comes to the edge of his box to meet a long ball and a defender heads to Woodrow who lofts the ball over the bar from about 30 yards
  • 8:10pm
    9 Huge chance for Clarke Oduor as a Jordan Williams left-wing cross finds him totally unmarked about five yards out but he mistimes his shot and scuffs it to the goalkeeper
  • 8:14pm
    A very positive start for the Reds. Both the wing-backs have put in good crosses which have led to excellent chances missed by Adeboyejo and Oduor
  • 8:14pm
    Josh Benson is the first man in the book after losing the ball then tripping a Bolton player up
  • 8:16pm
    14 Bolton corner on the right. Isgrove takes and Styles clears then Antoni Sarcevic's shot from 25 yards floats wide
  • 8:22pm
    Victor Adeboyejo, 23, is Barnsley's third oldest player tonight after Michal Helik, 25, and Cauley Woodrow, 26.
  • 8:23pm
    Midway through the first half. Barnsley started very brightly and missed two fine chances in the first ten minutes through Adeboyejo and Oduor. They are still dominating the ball but the game is a bit more even now
  • 8:28pm
    Barnsley keeping the ball really well. They just had it in the Bolton box for a good ten to 15 seconds but could not find a way through. They just need a bit more magic in the final third
  • 8:30pm
    29 Another chance for Adeboyejo. Jasper Moon wins the ball near halfway then Oduor plays in Victor but his shot from the edge of the box in plenty of space on the right is wide of the near post
  • 8:33pm
    31 Corner to Bolton on the left. Lloyd Isgrove takes it short then crosses but Helik heads clear
  • 8:34pm
    32 Big chance for the hosts. They attack again after the corner is cleared and Sarcevic gets the ball down the right then crosses low to George Johnston whose low shot from about ten yards is saved by Walton diving to his right
  • 8:36pm
    33 Now Callum Styles has a 25 yard shot which is deflected to the goalkeeper
  • 8:40pm
    38 Brilliant move from Barnsley. Benson turns away from a Bolton man on halfway then, after more skill from Styles, Woodrow unlocks the defence with a lofted ball but it is just slightly too far in front of Oduor and the goalkeeper gathers it
  • 8:42pm
    40 Another half chance for Sarcevic but he drags a shot well wide on the edge of the box after good work on the left
  • 8:43pm
    Callum Styles and Josh Benson are both playing well in the middle for the Reds, helping them dictate possession and regularly bursting forward with good runs – showing plenty of skills
  • 8:45pm
    Entering the final minute of the first half, plus stoppages
  • 8:47pm
    One added minute
  • 8:47pm
    HALF-TIME: Bolton 0, Barnsley 0. The Reds missed some fine early chances but the hosts have settled into the game and had some opportunities themselves.
  • 9:04pm
  • 9:05pm
    47 Isgrove free-kick on the right. Punched clear by his former Oakwell colleague Walton
  • 9:06pm
    48 Isgrove corner on the right. Ricardo Santos wins a header but sends it well wide
  • 9:10pm
    Barnsley yet to really settle in this second half and get into the rhythm that saw them dominate the ball in the first. Bolton have begun brightly after the interval
  • 9:11pm
    52 Clarke Oduor fires wide just inside the box after Liam Gordon gifted him the ball. That all came from another bullocking run by George Miller
  • 9:14pm
    Cameron Thompson is on for his professional debut. Adeboyejo off
  • 9:18pm
    58 Ex-Red Gethin Jones sees a powerful shot from a very tight angle on the right of the box beaten away by Walton
  • 9:19pm
    Devante Cole and Herbie Kane on for Cauley Woodrow and Callum Styles Barnsley fans have been chanting Cole's name to the tune of Gold by Spandau Ballet pretty much since half-time
  • 9:21pm
    61 Gethin Jones is causing problems for Barnsley. He gets down the right side of their box again and his low cross whizzes across the face of goal and is turned behind by Miller. Barnsley clear the corner but have been second best this half
  • 9:24pm
    Bolton bring on former Huddersfield and Sheffield Wednesday man Elias Kachunga on for Eoin Doyle
  • 9:26pm
    Midway through the second half. Bolton have been the better team after the break. They have only created a couple of half-chances and the Reds haven't controlled the game like they did for much of the first half.
  • 9:27pm
    Gethin Jones booked for bringing down Thompson on a counter attack
  • 9:30pm
    Michal Helik has been superb in defence tonight - a cut above. He's also trying to burst forward on the attack from centre-back whenever he can. Someone needs to make something happen if the Reds are going to win this in the 90 minutes.
  • 9:30pm
    71 Barnsley's first chance of the second half, Miller crosses and Devante Cole heads it about 12 yards out under pressure from a defender but it's very close to the goalkeeper who catches easily
  • 9:35pm
    'If Devante scores, we're on the pitch' from the away end
  • 9:35pm
    Into the final 15 minutes. Barnsley have been a little bit better recently, with the likes of Cole and Thompson adding impetus. Can they find a winner?
  • 9:37pm
    Bolton bring on Josh Sheehan for Kieran Lee
  • 9:41pm
    George Miller is up front now, has been struggling with cramp. Jordan Williams right wing back and Oduor on the left.
  • 9:44pm
    Into the final five minutes here. It's been a poor second half for the Reds, but can they pinch the win before the shoot-out?
  • 9:47pm
    Bolton still on top, pushing forward a lot but their crosses and final passes are either overhit or easily dealt with by the Reds
  • 9:49pm
    90 Walton makes a save from a shot on the edge of the box then is out jumped by Bakayoko who heads over the rebound
  • 9:49pm
    Three added minutes
  • 9:51pm
    90+1 Bolton corner on the right headed well wide by Santos under pressure from Helik
  • 9:54pm
    FULL-TIME: We go to penalties
  • 9:56pm
    Josh Benson will take the first penalty
  • 9:56pm
    Josh Benson SCORES 1-0 Barnsley
  • 9:57pm
    Antoni Sarcevic SCORES 1-1
  • 9:58pm
    Herbie Kane SCORES 2-1 Barnsley
  • 9:58pm
    Lloyd Isgrove SCORES 2-2
  • 9:58pm
    Michal Helik SCORES. 3-2 Barnsley
  • 9:59pm
    Amadou Bakayoko SCORES 3-3
  • 10:00pm
    Jordan Williams SCORES 4-3 Barnsley
  • 10:00pm
    Elias Kachunga SCORES 4-4
  • 10:01pm
    Devante Cole MISSES 4-4.
  • 10:01pm
    Joel Dixon dives to his left to save
  • 10:01pm
    Josh Sheehan SCORES. Bolton win the shoot-out 5-4