Replacing another ex-Wolves player in Rob Edwards after the Welshman stepped down from the club to take up a coaching role with the FA last week, Kennedy has been working with the under-23s during the last few weeks after joining the club in the summer.
His first task is to find a way to overcome a Derby side who knocked Wolves out of the same competition at the last-16 stage last season.
It’s the first match of the PL Cup for both Wolves and Derby, who are currently sat in second place in the Premier League 2 table, losing just one game in the league all season.
WHEN
Monday 7pm
WHERE
Pride Park, Derby
LAST THREE
Wolves
2-2 v Morecambe (A) LCT
1-2 v Southampton (H)
4-2 v Carlisle United (A) LCT
Derby
2-0 v Manchester City (H)
2-0 v AS Monaco (H) PLIC
1-0 v Blackburn Rovers (H)
WHAT THE BOSS THINKS
On a PL Cup rematch with Derby County
“Derby are a fantastic Academy, they’re always a very good team, and they did really well in the competition last year.
“I never look back, I always look forward, and I’m saying that as a coach who wasn’t here last year, but ultimately tonight is about Wolves, our players, and what we do, our approach to the game, while being incredibly respectful to Derby.”
On the approach to his first game in charge
“We will always do our homework on the opposition – where we think we create things and cause them problems, where we think their strengths are, what we need to do to combat them and where we think we can gain an advantage.
“That’s paramount to any level; under-23s, first-team and even under-18s, because you’re at the business end of football where they’re moving over from development to men’s football, where winning is paramount.
“We’ll do all of that, but our approach tonight is all about Wolverhampton Wanderers, our style of play and how we do things – that’s really important to us.”
NEXT FIVE
07/11 Derby County (A) PLC
20/10 Liverpool (A)
26/10 Tottenham Hotspur (H)
01/11 Derby County (A)
05/11 Blackpool (A)