Former Saints boss Dave Merrington will be involved in a charity fundraiser with ex-Pompey star Linvoy Primus and former AFC Bournemouth manager Lee Bradbury this week.
Totton Family Fun Day will welcome the trio to Testwood Baptist Church, Salisbury Road for an evening of football chat, from 7.30pm on Friday (April 11).
All the proceeds will go to Totton Family Fun Day, which received a Civic Award for its service to the community in 2013.
Event organiser John Cunningham said: "We believe having three of the south-coast's teams represented on the same stage may well be a first.
"It will be an evening of football anecdotes, banter, humour, chat and more. We're looking forward to the night and from reports so far, expect a good turn out."
Merrington, now a matchday summariser on BBC Radio Solent, managed the Saints during the 1995-96 season after several years as the club's youth team coach, a period in which he was responsible for the development of Alan Shearer and Matt Le Tissier, amongst several others.
Primus played in the Premier League during a nine-year spell with Pompey, where Havant & Waterlooville manager Bradbury began his career before playing for Manchester City and Bournemouth.
Bradbury began his managerial career with a 14-month spell in charge of the Cherries from January 2011.
Tickets will be available on the door, priced £7.50 (adults) and £1 (students), with a minimum age of 12.
Totton Family Fun Day is a free, annual event for all the family held in June and is part of the ongoing community activities of Testwood Baptist Church.