Jimmy Floyd Hasselbaink feels the Chelsea star could have done more (Picture: Getty)
Hayden Hackney’s 37th-minute strike was the difference for the Championship side with Caicedo failing to track the goalscorer’s run into the box.
Caicedo’s overall performance was far from impressive too, with the Ecuador international midfielder sloppy in his passing.
Speaking about Middlesbrough’s winning goal after the match, former Chelsea striker Hasselbaink told Sky Sports: ‘With Caicedo… It becomes a one-versus-one.
‘If you have determination, you don’t lose your one-versus-one. It’s a simple one.
‘You just keep running with your man, you stay with him, and at the last moment you give him a little nudge so he cannot put that ball in. He stopped!’
Moises Caicedo put in a poor performance as Chelsea lost the first-leg tie (Picture: Getty)
Speaking about Chelsea’s wastefulness in front of goal, with Cole Palmer missing several key chances, Hasselbaink added: ‘I felt there was a plan [from Chelsea] but they needed to do more to break the lines.
‘There needed to be unselfish runs to open the space up. You need to not put crosses in if you only have Raheem Sterling in the box.
‘It’s about know-how and understanding your team-mates. It didn’t happen enough with Chelsea. It was slow, it was laboured and there were too many turnovers for Boro to have joy.
‘And that’s why they were dangerous. It all starts with the right mentality. It starts with the right mindset. They didn’t put the opposition on the backfoot and they weren’t playing in the right areas.’