The 74-year-old spent six years as a Saints player and an extra six years in charge as boss, before moving to the Saddlers and spending three years as manager - earning them promotion from the old Division Three in 1995.
Nicholl now sadly suffers from dementia and after a spell living in Walsall he recently moved to assisted living in Southampton to be closer to family.
Wayne Thomas, who played under Nicholl at Walsall, organised the game at Rushall Olympic's Dales Lane through his Ace Academy and Ace Foundation.
Thomas said: "I started Ace Academy almost five years ago and a lot of what we do is with the younger generation and Chris has always come and helped us out.
"I wanted to start Ace Foundation for a few years because for some children, monthly subs, boots and everything you need is unattainable.
"We launched the foundation with the premise of trying to give kids opportunities and inspire them.
"I got the opportunity to become a professional footballer 25 years ago because of Chris. He inspired me.
"I didn't play for long but I played for a lot of good people and Chris stood out like a beacon, that's why I wanted him to become a patron.
"Sadly his health has deteriorated a little bit and I've stayed in contact with his family. They loved the idea of a game and it snowballed from there.
"Chris is a legendary manager for Walsall. He brought through a lot of kids that had good careers.
"He played for Northern Ireland, at the Villa and at the top level for Southampton.
"People hold him in the highest regard as a coach and a player. He's a winner and a legend."
Kick-off was delayed by 30 minutes on Friday night as the Southampton coach - filled with stars such as Matt Le Tissier and James Beattie - travelled for hours on the motorway for the clash.
Legendary former Walsall manager Ray Graydon was also in attendance, alongside Villa boss Dean Smith, who spent four years in charge of Walsall.
Former England international Le Tissier, who started his career under Nicholl at Southampton, spoke to the Express & Star after the match – paying tribute to his former boss.
He said: "Chris was fantastic for me, he was my first manager and I had him for the first six years of my career.
"He gave me my debut in the First Division and as a young 17-year-old lad he gave me my chance. I was in and out of the team for a couple years but those years were invaluable to me.
"You only have to look at how well Chris is respected by every club he played for and managed.
"At Southampton the fans held him in very high regard and as player he always gave everything he had for every club. That's all the fans ask for and that's why he's so popular. He gives you 100 per cent honesty.
"We travelled hours on the motorway to come for Chris and we'd do it again in a heartbeat because he's a genuinely lovely bloke."
Colin Cramb put Saints ahead but goals from Peter Till, Kevin Betsy and a Darren Byfield double secured the win for the Midlands legends.
Former Villa and Walsall striker Byfield was a constant menace for the opposition defenders as he netted his brace but he was just pleased to see so many people out to support Nicholl.
He said: "It's shown by the support with all the ex-players coming down, nothing would get in the way to support Chris. He's a top guy, top manager and top coach.
"He's always so respectful and he gets that same respect back.
"It's enjoyable to play these games. It's great for the fans to come out and support Chris. We've all been locked up so it's great for them to witness some football."
In the end, the results off the pitch were more important after around 800 fans came through the turnstiles - raising thousands of pounds for charity.
Thomas said: "It's difficult to say but hopefully, after costs, we'll have raised around £7,000 to £8,000. That would be fantastic.
"We've committed to making a 20 per cent donation to the Saints Foundation and we'll also sit down with the Nicholl family to decide where the money goes.
"Our foundation will also take a percentage and then if the Nicholl family would like to donate something to Dementia UK or to any other organisation, then that's what should happen."
They now hope to make it an annual event after the inaugural Chris Nicholl Trophy was won by the Midlands legends.
Thomas added: "They've travelled miles and deserve a massive round of applause for that. We've already spoken about doing it annually and maybe take it to Southampton so the Walsall fans can see the coast. Hopefully this game becomes bigger and better.
"We hope it can become an annual thing and we hope to do more things with the foundation for Chris."