The Blues are guaranteed to meet Championship opposition after this afternoon’s draw for the second and third round of the competition we last won in 2015 was made.
A meeting with Middlesbrough would of course be a rerun of the 1998 final, when goals from Frank Sinclair and Roberto Di Matteo secured the trophy for Gianluca Vialli’s Blues. We last played Boro in May 2017 on a night which condemned them to relegation to the Championship, where they have been ever since. They beat Shrewsbury 4-3 on Friday to book their place in the second round.
Barnsley meanwhile dramatically survived relegation to League One in the final minute of last season, and started this campaign with an impressive 1-0 Carabao Cup victory over Nottingham Forest yesterday.
We last met the Tykes in March 2008, when they shocked us in the FA Cup quarter-finals, winning 1-0 at Oakwell. Should they beat Middlesbrough, it will be their first visit to Stamford Bridge since January 1998.
The tie will take place the week commencing Monday 21 September, between our Premier League fixtures at home to Liverpool and away to West Bromwich Albion. Middlesbrough meet Barnsley at the Riverside Stadium a week before.