With four matches taking place on what should be a spooktastic night, one is a London derby whilst Frank Lampard and Tony Pulis both meet former clubs as they aim to produce cupsets.
Blackpool are going well in League One but this is a tough match because Arsenal are currently flying, having not lost in any of last 11 games.
Throw in their poor away record of no wins in last 14 visits to Arsenal who have knocked out non Premier League opposition at this stage in last two seasons, then I can see just one result coming here.
Prediction: Arsenal 3-0 Blackpool
Result: Arsenal 2-1 Blackpool
Frank Lampard is right in believing that his Derby side can cause yet another cupset but this time, on his former home turf as he returns to Stamford Bridge for first time as a manager.
Given that both teams have returned from international break in strong form, I am expecting a fierce battle here despite both having higher priorities elsewhere competition wise.
Chelsea are certainly going to make changes and have handed The Rams permission to field loanees, Mason Mount and Fikayo Tomori. That is a bold risk because they could very well put their parent club out and my gut feeling is telling me that will happen.
Prediction: Chelsea 1-2 Derby County
Result: Chelsea 3-2 Derby County
Having only played 48 hours previously come kick off, Tottenham face a tough test as they face a West Ham side targeting a cup run.
The Hammers however are also expected to field a weakened side featuring some youngsters making this a tough one to call.
Spurs just edged their league meeting here 11 days ago but aren’t the most strongest attacking side at present, whereas West Ham are inconsistent with just two clean sheets all season which both came at home.
A draw therefore would be decent but West Ham don’t tend to do draws and Spurs’ fitness might slide as match wears on as a result of two matches in three days. For that reason, I am going for a tight home win here.
Prediction: West Ham United 2-1 Tottenham Hotspur
Result: West Ham United 1-3 Tottenham Hotspur
This is really the ‘Tony Pulis derby’ as Middlesbrough welcome one of his former sides, Crystal Palace to the Riverside Stadium.
Palace have struggled so far this season apart from in this competition when they have kept two clean sheets in two away ties but there are various omens going against both teams winning this tie.
Pulis has only progressed from one of five matches at this stage as a manager whilst Eagles boss, Roy Hodgson is yet to even win at the Riverside Stadium and Palace have only reached the League Cup Quarter Finals once in last 15 attempts.
If we do get a winner, it will be because Crystal Palace put out a strong team like they did against Swansea and West Bromwich Albion in last two rounds. I however can see a draw coming and penalties being needed.
Prediction: Middlesbrough 1-1 Crystal Palace (Middlesbrough win on penalties)
Result: Middlesbrough 1-0 Crystal Palace