Portsmouth dumped Derby out of the League Cup as the League Two side claimed a shock 2-1 win at Fratton Park. Adam McGurk headed Pompey ahead as Derby stopper Lee Grant let the ball squirm through his hands. Jason Shackell then equalised for the Rams with a header from Johnny Russell’s corner. But, just three minutes later 18-year-old Conor Chaplin restored the hosts’ lead as he converted Enda Stevens’ perfect cross and they held on for a fantastic victory.

Doncaster scraped past Yorkshire rivals Leeds on penalties at the Keepmoat Stadium. Lewis Cook netted the 100th goal of the 2015-16 Capital One Cup to give Leeds the upper hand inside 14 minutes. But Andy Williams equalised from the spot after Scott Wooton brought down Cedric Evina inside the box. 18-year-old Wood was then sent off for a two-footed challenge on Aaron Taylor-Sinclair. The two sides were deadlocked for the rest of the match, including extra-time. Sam Byram and Chris Wood both fired their kicks over the bar, and Richie Wellens hit the winner for Doncaster.

Middlesbrough had no problems in getting through to the second round as they comfortably beat Oldham. Yanic Wildschut opened the scoring for Boro in the 23rd minute, before Christian Stuani headed in his first goal for the club. The Uruguayan forward then added a second, turning home James Husband’s low cross. Danny Philliskirk netted a late consolation goal for the League One outfit.

Oldham Athletic v Middlesbrough - Capital One Cup First Round

Preston also advanced to the second round as they beat Crewe 3-1 at Gresty Road. Jordan Hugill converted from the penalty-spot and Will Keane scored his first competitive goal for the club to give Preston a two-goal lead inside 13 minutes. The home side pulled a goal back nine minutes before the break as Adam King converted Bran Inman’s cut-back. But Josh Brownhill confirmed Preston’s place in the second round draw with a volley from the edge of the box.