London derby if we beat Barnsley

The draw was made tonight (Thursday) in advance of the third round fixtures to help with scheduling and broadcast arrangements, with the tie due to take place the week commencing 28 September.

League Two Leyton Orient came from 2-0 down at home to Plymouth to win 3-2 in the second round and book a meeting with Jose Mourinho’s Tottenham a couple of days before their Europa League third round qualifier away to Macedonian side Shkendija.

Fourth round ties will be played the week commencing 28 September. If Tottenham beat Shkendija, they would have a Europa League play-off to contend that midweek.

We last played Leyton Orient in 1982 in the old Division Two, that game a 2-2 draw at the Bridge. We won 2-1 at Brisbane Road earlier in the season. We have never met the O’s in this competition. 

The same cannot be said of Tottenham. We last played them in the Carabao Cup in January 2019, winning that semi-final tie on penalties after the two legs couldn’t separate the sides.