Town’s U21s are in Professional Development League Two South action against AFC Bournemouth at the Vitality Stadium this evening (KO 7pm).
The young Blues are currently fifth in PDL2 South with the Cherries second and on a 12-game unbeaten run.
A crowd of around 2,000 is expected at the Vitality stadium to see the Blues’ youngsters take on the Cherries, who are coached by Town academy alumnus Alan Connell.
The former striker was at Playford Road in the early 2000s - when Town U21s coach John McGreal (pictured) was a regular in the senior side - before moving on to Bournemouth for the first of two spells as a player, while he also spent time at Torquay, Grimsby, Swindon, Northampton, Hereford and Brentford during a career in the lower leagues.
Connell, 40, will be facing Town for the first time since he left the academy just over 20 years ago.
"I had two great years there and feel very fortunate to have learned my trade as a young player at that club and at that time,” he told the Cherries official website.
"My apprenticeship, as it was then, was between 2000 and 2002 which coincided with the last two years Ipswich were in the Premier League.
"I was fortunate to watch some great games and to get to train with the first team which was something I did quite a lot during my time there. That was a really valuable learning experience for someone who was as young and keen as I was.
"As a club, it was all about developing, improving and learning. I learned so much from great people like Bryan Klug, Paul Goddard, Ken Goody and Simon Milton, people who have been synonymous with Ipswich over the years.
"I did everything I could to have a career as a professional footballer and will always be extremely grateful for the environment, platform and opportunity that Ipswich provided for me.
"Although I never broke into the first team, it set me up well for my next step which was joining AFC Bournemouth in 2002.
"It’s remarkable to think this is the first time I will have crossed paths with them since then.
"As a player, they were always in a higher division and, in nine years coaching here, I have never come across them, not even in a friendly.
"Now we have been elevated to category two, this is the first opportunity for me to go against a club I learned so much at some 20-odd years ago.”