Now, in an unusual change of circumstances, Watson, who scored the winner in the 2013 FA Cup final against Manchester City, has returned the favour by dotting the i’s and crossing the t’s – as he is Maloney’s agent.
Cup fever will once again return to Wigan on Monday when the League One side take on Manchester United at the DW Stadium.
Maloney, 40, who spent four years as a Latics player, is now the club’s boss and is hoping to pile more pressure on United manager Erik ten Hag.
And watching from the director’s box will be Watson who, after quitting the game, now works as a registered football intermediary for CAA Base in tandem with experienced agent Anthony McFarlane.
Watson, who retired after leaving Charlton in 2022, said: “Shaun has been a friend for a long time and that is the reason we work together. I still go up and watch Wigan’s games quite a lot as he is a client.
“I am learning every day. I started working for Base as they represented me for 20 years. It was a thing which always interested me and I got into it this summer.
“I was represented by Anthony, who also looked after Shaun. Now, me and Anthony work together and I am learning off him every day.
“Agents get a bad name because there are a handful of them who have caused some problems. But agents can be very important and a lot of good things come from those who work hard and are honest.
“I think if you have been a player, it is a great selling point if you want to represent someone.
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“I am looking out for the best up and coming talent. My son, Reggie, plays for Crystal Palace under-14s and if I also wanted someone to represent my son, I would want someone who had been in the game.”
Against United, Watson is hoping Maloney can help deliver yet another huge shock against a Manchester club.
It was Maloney’s injury-time corner which fell perfectly for Watson to score with a glancing header against City at Wembley in a result which stunned the world of football.
Watson, 38, said: “It is a game that comes up every year. It always gets mentioned, every time you see a few FA Cup goals from the past. Certainly nine times out of 10.
“It was a special day. A day any player dreams about. You dream about being in a final but to score the winner was surreal. It was an incredible achievement for myself and the club
“Once you score a goal like that, you know you will be part of history forever. It was one of the great shocks in sporting history. You ask anyone to name five players from that Wigan team and they might struggle but look back at that City team and you had Tevez, Aguero, Silva, Toure and Kompany, all legends of the Premier League. In their eyes, they just had to turn up and roll us over.
“For the goal, I should not have been in the area to start with and was supposed to be on the edge of the box. But because they were down to 10 men, I drifted in and because they were zonal marking, I got a free run. I did not score many headers and it was a good job Aguero was on the post as anyone taller might have had a sniff. It was like it was meant to be.
It had been a difficult season for me due to injury and I did not play a single second in any of the previous rounds.
“We got relegated 72 hours later but Wigan winning the FA Cup was something that can never be taken away.
“The real success at Wigan was down to Dave Whelan, a fantastic guy who only cared about the football club of Wigan and the town of Wigan.
“The club has been in the hands of different owners who may not have had the same love but now Mike Danson has come in and steadied the ship.”
So, could Wigan deliver a huge shock against United?
Watson said: “It will be the first time since the Premier League era that the stadium will have been a sell-out. United are going through a sticky patch and Wigan have got to make it tough.
“The fans will know they have to create a good atmosphere for Shaun and the players.”