Maradona and Messi are Argentina's two greatest footballers - both have very strong cases to be the best ever to have played the game - and everywhere the Barcelona star seems to be, the controversial yet brilliant ex-player seems to follow.
Messi has won almost every big honour there is to win in the game but the greatest title of them all still alludes him to this day, the World Cup.
Maradona claimed football's biggest prize in football back in 1986 in Mexico and there is no one out there as desperate as him to see Messi lift the World Cup before he hangs up his boots.
The flambuoyant 57-year-old showed his huge support and love for his compatriot on Thursday before the Croatia match by proudly hanging up an Argentine 'Messi' shirt over the railings.
The whole of Argentina were wishfully hoping Maradona's presence would inspire Messi and Co to victory against Croatia... but it wasn't to be and they are now on the brink of elimination at the World Cup following their humiliating 3-0 defeat.
But despite Argentina's latest setback, Maradona will certainly not shy away from supporting Messi and his beloved country.
Maradona - scorer of arguably the best goal in World Cup history against England in 1986 - has followed Messi everywhere he has gone since making his debut in the tournament, whether that be in a supporting or coaching capacity.
In 2006, an exciting, young and floppy-haired Messi burst onto the World Cup scene against Serbia, where he assisted Argentina's fourth strike and scored their final goal in a 6-0 rout after coming on as a substitute.
Maradona witnessed the start of something special against Serbia and was also in attendance against Holland and Mexico before they were knocked out in the quarter-final stage by Germany. His apprentice had arisen on the international stage.
After watching him from the stands, it was then time for Maradona to witness Messi's talent first-hand as he managed the squad at the 2010 World Cup in South Africa.
Maradona led the Argentine's to the quarter-finals, where they were knocked out yet again 4-0 by Germany.
But after opening wins against Nigeria and South Korea, in which Messi starred by having a helping hand in all four goals, Maradona decided to give his star man the huge responsibility of captaincy against Greece as he rested some of his main players.
Under Maradona's management, Messi worked his magic in the round of 16, conjuring up an assist for Argentina's first goal as they beat Mexico 3-1.
Out of the four World Cup's Messi has participated in, the 2014 tournament in Brazil was the only one where the five-time Ballon d'Or winner didn't have the pressure of Maradona hanging over him.
And it appeared to pay off with Messi and Co reaching the final, the closest he has ever come to claiming the biggest prize in world football.
But, they came up against their bogey team Germany in the highly-anticipated showdown, with Mario Gotze netting an extra-time winner.
So where was Maradona? Well the football icon was busy taking up his pundit duties for TV, in which he said he would lay out the 'red carpet' for Messi if he won the World Cup.
The only match Maradona attended as a fan that summer was against Iran, in which Messi scored a spectacular injury-time goal in the 1-0 win.
But it was telling that summer... with Maradona busy at work, Messi propelled Argentina to the final and won the Golden Ball.
And fast-forward four years to the present, Messi's World Cup struggles have re-emerged and Argentina are in a precarious position with just one group game remaining.
Maradona has been his charismatic self in the stands, keeping a close eye on his fellow Argentine great, but Messi has under-performed with the weight of expectation firmly on his shoulders.
While Messi has been let down by his team-mates, the 30-year-old hasn't been his normal self, missing a penalty in the 1-1 draw with Iceland before being kept limited as Argentina were crushed 3-0 by Croatia.
With Argentina on the brink of further humiliation, it's time for Messi to stand up and be counted.
With this likely to be Messi's last World Cup, it's also time for him to make Maradona the proudest man in football.