Promotion-chasing Middlesbrough conceded a 96th-minute equaliser in a 1-1 draw against Bristol City at Riverside Stadium.
Castledine swept in Hayden Hackney’s pass to net the 65th-minute finish to put Boro ahead, until Adam Randell headed in a 96th-minute equaliser from Tomi Horvat’s corner.
Middlesbrough remain second in the table and now seven points off the summit after leaders, Coventry lost 2-1 at home to Southampton, whilst Bristol City stayed 12th in the table.
Winless in their last eight meetings against Bristol City and coming into this game off the back of a surprise midweek defeat to Charlton, Middlesbrough continued to lack a polished final touch to their dominant possession-based play.
That absent finishing quality was evident in the ninth minute as Hackney whipped in a cross, which Tommy Conway headed over the bar against his old club.
Luke Ayling then flicked a 19th-minute shot wide of his near-left corner after he met Hackney’s cross towards the left post, after the midfielder was involved in a short corner played around the edge of the box on the right side of the pitch.
Boro continued to enjoy dominance in possession but Bristol City stood firm defensively despite a lack of notable attacking threat to pressurise the hosts’ Sol Brynn before half time.
Bristol City eventually found their first proper shot of the game in the 52nd minute after Emil Riis Jakobsen was played forward, but he was only able to rifle his low shot wide of the left corner.
Radek Vitek then spared Bristol City’s blushes in the 55th minute as he blocked Aidan Morris’ 55th-minute shot, before he then made a goal-line save to deny Alan Browne’s close-range rebound strike.
Boro’s pressure eventually proved too much as Hackney found space to play a 65th-minute square-ball pass which Castledine turned in past Vitek’s reach to put the hosts in front.
Bristol City were lucky to not concede a second goal in the 81st minute after a defender flicked the ball behind him which David Strelec latched onto, yet the Slovakian smashed his shot straight into Vitek who made a crucial block.
Boro eventually were denied a first win over the Robins since August 2021 as Randell thumped a 96th header into the top-left corner to rescue the visitors a point.
What’s Next?
Middlesbrough will again be in action at lunchtime on Saturday 21 March as they visit Blackburn in a 12:30pm GMT kick-off at Ewood Park.
Bristol City meanwhile host relegation-battling West Brom at Ashton Gate later that afternoon in a 3pn GMT kick-off.
Teams
Middlesbrough: Sol Brynn, Callum Brittain, Luke Ayling, Adilson Malanda, Matt Targett, Aidan Morris, Jeremy Sarmiento (Castledine 60′), Hayden Hackney (Gilbert 72′), Alan Browne, Riley McGree (Strelec 59′), Tommy Conway (Edmundson 90′)
Substitutes: Leo Castledine, George Edmundson, Alex Gilbert, Sontje Hansen, Fin Munroe, David Strelec, Kaly Sene, Morgan Whittaker, Joe Wildsmith
Bristol City: Radek Vitek, Sam Morsy (Hovrat 82′), Noah Eile, Cameron Pring, Marc Sykes, Jason Knight, Adam Randell, Ross McCrorie, Scott Twine (Bird 78′), Emil Riis Jakobsen, Sinclair Armstrong (Bell 68′)
Substitutes: Sam Bell, Max Bird, Louie Derrick, George Earthy, Daniel Ezendu, Tomi Horvat, Joe Lumley, Seb Naylor, Marley Thelwell
Referee – Stephen Martin
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