FA Cup
Boro, eighth in the second-tier Championship, followed up their fourth-round win over Manchester United by defeating Tottenham Hotspur 1-0 on Tuesday.
Manchester City visit Southampton in an all top-flight encounter, while Liverpool are assured of Championship opposition after being drawn on Thursday against the winner of Nottingham Forest and Huddersfield, who play on Monday.
Crystal Palace will face Everton. (The Toffees ousted non-league side Boreham Wood 2-0 thanks to a Salomon Rondon double after the draw was made earlier in the evening).
Quarterfinal ties will be played over the weekend of 18-21 March.
Crystal Palace v Everton
Nottingham Forest or Huddersfield v Liverpool
Middlesbrough v Chelsea
Southampton v Manchester City
Ties to played on the weekend of March 18-21
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