Gareth Taylor’s young Blues facing a testing fifth round assignment away at high-flying Derby County Under-18s on Thursday night.
The tie, which takes place at Pride Park, will see City tackle a Derby side that has recorded nine straight victories in all competitions, a run which has lifted the Rams up into second place in the Premier League Under-18s table.
Like City, Derby are also through to the semi-finals of the Premier League Under-18s Cup.
Redmond famously skippered the Blues to our maiden FA Youth Cup triumph back in 1986, an achievement which helped provide him with one of the most memorable moments of his career.
And he believes the lure of achieving success in the blue-ribbon event will burn just as bright with the current Under-18s squad.
“Coming through at 16,17,18 in the FA Youth Cup, it’s like the FA Cup now for the first team - everyone wants to win it,” said Redmond.
“We were fortunate enough to do that and it’s a great memory for the lads who were involved.
“I’ve still got my trophy in my cabinet back home, I look at it every now and then and I look at it with pride because I didn’t win many so it’s one that stands out in the cabinet.”
Back in the mid-1980s, Redmond was part of a richly-talented City side which also featured several other prodigious homegrown talents such as Paul Lake, David White, Andy Hinchcliffe and Paul Moulden.
What made our triumph all the more memorable was that it was achieved against Manchester United with the boy Blues securing a 3-1 victory on aggregate.
And with several members of City’s current Academy squad having been given a taste of first team football already this season in addition to the emergence of Phil Foden, Redmond says there are several uncanny parallels.
“Back in the day we knew we were decent players at the time but the group of lads that went on to win the FA Youth Cup – I think Tony Book and Glyn Pardoe, our manager at the time, I think they knew deep down we had every chance of winning at the start of the competition,” Redmond reflected.
“I think as lads we didn’t realise how good we were – we went on to beat Man United in the final over two legs.
“We got eight or nine players playing in the first team, it just wasn’t really heard of in those days – obviously very special and it’s great to see the young local lads coming through the system again.”