The very first Charlie Stillitano Cup was given to the winner of the Chelsea FC v Manchester City FC match held at Yankee Stadium on May 25, 2013. Manchester City won the "CSC" (alternatively called The Charlie Stillitano Trophy) by a score of 5-3

At the Charlie Stillitano Cup, Rog met SiriusXM FC caller "Andrew from Toronto" and this was referenced on the MIB SiriusXM FC show of May 31, 2013. Davo thought it was amazing that the players played as hard as they did during the match. The match made Rog break out into the West Side Story song "America" during the broadcast and at that point both Rog and Davo attributed alternating singers and lyrics with current EPL players.

And finally, Rog met Lady Physio at The Charlie Stillitano Cup

The Charlie Stillitano Cup is also used in reference to The Guinness International Champions Cup, where Real Madrid beat Chelsea 3-1 on August 7, 2013 in Miami, Florida.

In 2014, Manchester United beat Liverpool 3-1 in Miami, Florida, after going down 0-1 in the fifth minute.