Chelsea qualified for the League Cup semifinals thanks to a dramatic late show and penalty kick shootout against Newcastle United last night, and our reward for those heroics is the easiest possible draw, at least on paper.
We will be facing the only remaining second division side in the two-legged (again, for some reason) semifinals, which will be played January 9 or 10 (away) and January 23 or 24 (home).
Then again, Middlesbrough, under the guidance of former Manchester United player Michael Carrick didn’t make it this far by accident, though they did get quite lucky in not having to face any Premier League sides — until now. They beat Port Vale of the third division in their quarterfinal, 3-0.
We last played Middlesbrough in the quarterfinals of the 2021-22 FA Cup, winning 2-0 thanks to goals from Romelu Lukaku and Hakim Ziyech. That feels like a lifetime ago.