Middlesbrough scored two stoppage-time goals as they won 3-1 at Bolton to book their place in the third-round of the Carabao Cup.
Wanderers went ahead midway through the first-half at the Toughsheet Community Stadium as Dion Charles - fresh from signing a new contract with the club - scored from close range on the rebound, but Boro were level at the break after Matt Crooks broke the offside trap to loop a shot beyond goalkeeper Joel Coleman.
Michael Carrick's side were by far the better side after the restart but just couldn't make their dominance count, until the first of five added minutes when substitute Riley McGree pounced to make it 2-1, moments before fellow sub Morgan Rogers added a third for good measure.
As has become customary in the Carabao Cup, Ian Evatt made seven changes to the side that took to the field at Burton Albion on Saturday as Jack Iredale, George Thomason, Gethin Jones and Charles were the only ones to retain their places.
Even with nine substitutes available, the manager still decided not to name either Declan John or Kieran Sadlier, further fueling speculation over their futures as Thursday's transfer deadline looms.
With the action underway, it took Wanderers just seven minutes to get themselves on top as Josh Sheehan and Carlos Mendes Gomes combined to free Charles, whose appeals for a penalty were rejected by referee Stephen Martin.
Charles did find a breakthrough midway through the half, though, as he pounced from close range to give the hosts an advantage against their Championship opposition.
The goal arrived at the end of a move which had seen Jones cut the ball back for Sheehan, whose first-time cross-shot was parried by Boro goalkeeper Tom Glover into the path of Charles, who took one touch to compose himself before slotting into an empty net.
The visitors were level 10 minutes later, however, as Paddy McNair's through ball caught the Wanderers defence napping, allowing Crooks to run clear and send a looping shot beyond Coleman to make it 1-1.
Aaron Morley came close with two efforts in as many minutes as Bolton looked to restore their lead - first seeing a deflected strike bounce wide, moments before a blistering effort after a well-worked corner ripped the side-netting.
Middlesbrough stepped up a level in the closing stages of the half and should have scored when Crooks opted to square for Marcus Forss when it was perhaps better to go alone.
Coleman made a save from Emmanuel Latte Lath, before making another in added time to deny Hayden Hackney, ensuring the sides went in level at the break.
There was one change in personnel as the players returned for the second-half, with Coleman, who had received treatment just prior to the interval, was replaced by Nathan Baxter - the first substitution involving a Trotters goalkeeper since May 2018, when Mark Howard came on in place of Ben Alnwick in a memorable 3-2 final-day victory over Nottingham Forest.
The second period was very much a slow burner, with nothing in terms of goalmouth activity in the early exchanges but no less than four yellow cards brandished by referee Martin.
Isaiah Jones and Crooks were booked in quick succession for Boro, who were soon followed by both Forrester and Thomason as Bolton looked to halt a number of dangerous counter attacks.
Iredale would join them midway through the half, sandwiched between changes which saw Evatt withdrawn the aforementioned Forrester and Thomason - as well as Mendes Gomes, as Jon Dadi Bodvarsson made another step on his return to active first-team duty.
Eoin Toal, who was making his first appearance of the season, denied Boro a certain goal with some last-ditch defending with 17 minutes to play, shortly before Charles had the chance to give Wanderers a late lead - the ball ultimately being stuck at his feet with the goal at his mercy.
With no extra-time at this stage of the competition and penalties looming, Middlesbrough upped the tempo in the final 10 minutes and came close on a number of occasions.
Samuel Silvera forced Baxter into action at his near post on 83 minutes, while Toal was in the right place to prevent a certain goal from the next attack as three opposition forwards were ready in behind.
Kyle Dempsey performed similar heroics in the final minute of normal time after Rogers had drifted inside to shoot, before Boro struck the crossbar as McNair's goalbound attempt was deflected onto the woodwork.
Boro's pressure eventually told in the first minute of stoppage-time as McGree found the bottom corner from distance to make it 2-1, before the visitors took full advantage of some tired defending from Zac Ashworth as Rogers added a third in the final minute.
Defeat means Middlesbrough will be in the hat for Wednesday's third-round draw - with Premier League clubs competing in European competition set to enter - while Bolton will be left to concentrate on league action - aside from the defence of their EFL Trophy, which begins against Salford City next Tuesday.
Before then, however, is the visit of Derby County, who will have had a free week to prepare for Saturday's fixture after being eliminated from the Carabao Cup in the previous round.
Bolton Wanderers: Coleman (Baxter 45), Iredale, Toal, Forrester (Dacres-Cogley 62), Ashworth, Thomason (Bodvarsson 70), Morley (Dempsey 80), Jones, Sheehan, Mendes Gomes (Maghoma 70), Charles
Subs Not Used: Nlundulu, Adeboyejo, Williams, Jerome
Booked: Forrester, Thomason, Iredale, Ashworth
Goals: Charles 23
Middlesbrough: Glover, McNair, Fry, Lenihan, Engel, Crooks (Rogers 78), Barlaser, Hackney, Forss (Silvera 73), Latte Lath (Coburn 85), Jones (McGree 85)
Subs Not Used: Jones, Gilbert, Howson, Payero, Bilongo
Booked: Jones, Crooks
Goals: Crooks 33, McGree 90+1, Rogers 90+4
Referee: Stephen Martin
Attendance: 8,624
Pos | Team | Pld | Pts |
1 | Portsmouth | 19 | 42 |
2 | Bolton Wanderers | 18 | 39 |
3 | Oxford United | 18 | 36 |
4 | Stevenage | 20 | 36 |
5 | Peterborough United | 19 | 35 |
View Full Standings >> |
Who is Bolton's 2022/23 Player of the Year? | |
---|---|
25.9% | Conor Bradley |
22.3% | James Trafford |
20.09% | Dion Charles |
10.05% | Kyle Dempsey |
6.82% | Aaron Morley |
6.45% | Ricardo Almeida Santos |
3.5% | George Johnston |
3.32% | Eoin Toal |
1.01% | Kieran Lee |
0.55% | Gethin Jones |