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Portsmouth match-winner Conor Chaplin is on a season-long loan from Middlesbrough's promotion rivals Ipswich Conor Chaplin scored a stoppage-time winner as Portsmouth stunned Middlesbrough to boost their Championship survival hopes and deal a huge blow to the Teessiders' automatic promotion bid. On-loan Ipswich forward Chaplin struck in the seventh minute of time added on from Adrian Segecic's corner to score from Portsmouth's only shot on target at the Riverside Stadium. Middlesbrough have slipped to fourth place in the table and are three points behind second-placed Ipswich, having played two games more. Chaplin's late, late winner will have pleased his parent club but perhaps not as much as it delighted his current side - it hauled Portsmouth back out of the bottom three and they are a point clear of Oxford with a game in hand. The defeat further damages Middlesbrough's hopes of going up automatically - Kim Hellberg's side have now managed just three points from their past six games, their worst run of the season. This was a proper smash and grab raid by Portsmouth and as poor as Middlesbrough were, they still managed eight shots on target. But they could not beat Pompey goalkeeper Nicolas Schmid as John Mousinho's Pompey side ended their eight-game run without a win at a critical time. Schmid saved a shot from Alan Browne and a weak header from Dael Fry in a fairly pedestrian first half. Hellberg tried to inject some vigour into his Middlesbrough side, bringing on Sontje Hansen and Luke Ayling at half-time, and Riley Mc Gree had a shot from a narrow angle saved by Schmid. The goalkeeper was in no mood to be beaten and he denied Browne, when the midfielder attempted to chip him, before he frustrated Mc Gree again. Middlesbrough pressed desperately to find a way through and Hansen had a shot saved before Andre Dozzell headed his second effort off the line in the first minute of stoppage time. The home fans urged their side on but it was Portsmouth who broke the deadlock thanks to Chaplin's second goal of the season, a strike that could have a massive impact at both ends of the table come the final reckoning. Middlesbrough boss Kim Hellberg told BBC Radio Tees: "We were not good enough. We lacked energy, quality and structure. "That is different from other games. Sometimes we played well without the result, today we were not good enough except defensively. It makes you flat and disappointed. "We didn't have our best game. We played three in a week, some games are better than others. We didn't defend the second phase of the corner well enough. That has been a theme of the home games. "Six in a row without a win from a team that plays good football. That is not a feeling you want, we are trying to make it right but we are not succeeding. That is my responsibility. " This video can not be played Hellberg: Boro 'not good enough' against Portsmouth Portsmouth manager John Mousinho told BBC Radio Solent: "Managing to score with the last kick in the circumstances is right up there [for most dramatic wins of my career]. "We did what we had to do today. We stayed in the game and had good opportunities on the break in the second half, we didn't have the confidence or belief. "When you don't have a lot of the ball it can sometimes be a bit panicked when you win it back. "Some of the last-ditch defending [was brilliant]. It was a whole team effort. " This video can not be played John Mousinho: 'That performance was up there' After the opportunity to rate players has closed, the score displayed represents the average from all the submissions by BBC Sport users. Comments can not be loaded To load Comments you need to enable Java Script in your browser Last Updated 11th April 2026 at 16: 58 Please Note: All times UK. Tables are subject to change. The BBC is not responsible for any changes that may be made. Manager: Kim Hellberg Formation: 4 - 2 - 2 - 2 Manager: John Mousinho Formation: 4 - 2 - 3 - 1 Manager: Kim Hellberg Formation: 4 - 2 - 2 - 2 Manager: John Mousinho Formation: 4 - 2 - 3 - 1 Championship All competitions All competitions All competitions Middlesbrough have won just one of their last nine league games against Portsmouth (D5 L3), a 3-1 away win in March 2012. Following their 1-0 win in October, Portsmouth are looking to complete the league double over Middlesbrough for the first time since 1993-94. Middlesbrough are winless in their last five Championship games (D3 L2), their longest run of the season. Since the date of that first winless game, they’ve had 48 more shots than any other side (126) and 122 more touches in the opposition’s box than anyone else (272). Despite this, they’ve only scored four goals and have the worst shot conversion (3. 2%), underperforming their x G by 8. 9 (4 goals, 12. 9 x G). Portsmouth have gone eight Championship matches without winning (D3 L5), their worst winless run since failing to win their first nine games of 2024-25. Middlesbrough’s Hayden Hackney has created the most chances both overall (83) and in open play (62) in the Championship this season. He’s also completed 848 passes in the final third, the fourth-most by a player in a Championship season (excl. play-offs) on record since 2013-14. Match ends, Middlesbrough 0, Portsmouth 1. Marlon Pack (Portsmouth) is shown the yellow card. Second Half ends, Middlesbrough 0, Portsmouth 1. Goal! Middlesbrough 0, Portsmouth 1. Conor Chaplin (Portsmouth) left footed shot from the centre of the box to the centre of the goal. Assisted by Adrian Segecic following a corner. Attempt missed. Adrian Segecic (Portsmouth) left footed shot from outside the box is close, but misses to the right following a corner. Corner, Portsmouth. Conceded by Alan Browne. Offside, Portsmouth. Millenic Alli is caught offside. Dael Fry (Middlesbrough) is shown the yellow card for a bad foul. Foul by Dael Fry (Middlesbrough). Colby Bishop (Portsmouth) wins a free kick in the attacking half. Substitution, Middlesbrough. Cruz Ibeh replaces Tommy Conway. Luke Ayling (Middlesbrough) wins a free kick in the defensive half. Foul by Colby Bishop (Portsmouth). Attempt missed. Aidan Morris (Middlesbrough) left footed shot from outside the box misses to the right following a corner. Corner, Middlesbrough. Conceded by Nicolas Schmid. Attempt saved. Sontje Hansen (Middlesbrough) right footed shot from the centre of the box is saved in the top right corner by Nicolas Schmid (Portsmouth). Fourth official has announced 6 minutes of added time. Corner, Middlesbrough. Conceded by Marlon Pack. Colby Bishop (Portsmouth) is shown the yellow card. Callum Brittain (Middlesbrough) wins a free kick in the defensive half. Copyright © 2026 BBC. The BBC is not responsible for the content of external sites. Read about our approach to external linking.