And it is fair to say it was an absolute disaster.
Nani missed a penalty, got booked and was hauled off in the 77th minute in a game against minnows Arouca, as Sporting Lisbon toiled without the suspended William Carvalho at the Jose Alvalade.
But interestingly, while the presence of one United player and absence of a well known apparent target was detrimental to Sporting's performance - a forgotten United target proved to be their hero.
Carlos Mane was linked with Manchester United for much of last season. His performances for Sporting had tongues wagging around Europe, so Sporting even gave him a new contract which contained a €45 million release fee.
He even spoke about the apparent interest at the start of the year, stating:
"It's always good to know that big clubs are interested in us, but now I'm focused on my selection at under-21."
And where Nani failed Mane thrived. He entered the field at half time and went on to score the winning goal for Sporting with one of the final kicks of the game ... to show Nani how it is done.
Should United keep tabs on Mane?