04:05 BST, Thursday 26th July, Rose Bowl (Pasadena, California, USA)
Gennaro Gattuso and Jose Mourinho take their clubs across the pond as both sides begin their International Champions Cup pre-season campaigns.
The Red Devils have already been Stateside for a short while and have played exhibition matches with Mexican side Club America and MLS' own San Jose Earthquakes.
United are yet to register a win on their travels, however, after being held to draws by both opponents, whilst Milan registered an early run-out win over fellow Italian side Novara.
The ICC has given a lift and importance to top clubs' pre-season preparations and both sides will want to get their campaigns off to a positive start on the west coast.
Last Time Out
AC Milan 2-0 Novara
Before embarking on their US trip, Gattuso's men played a rather subdued fixture with Novara in the small Italian commune of Carnago.
Novara faced the Rossoneri on the back of a dismal season which saw them relegated to Serie C after finishing bottom of the Italian second tier.
Gattuso's side ran out 2-0 winners after two first half goals from ex-Liverpool man Suso, and Davide Calabria in a game that will serve only the purpose of getting minutes in the legs before a tougher run-in to the start of the season.
Manchester United 0-0 San Jose Earthquakes
Jose Mourinho's side played out a dour 0-0 draw at Santa Clara's Levi's Stadium against MLS outift San Jose Earthquakes.
It was the Red Devils' second fixture on their US tour, though having drawn both of their opening fixtures, Mourinho will be eager to get a win on the board soon.
The Portuguese elected to play a relatively experienced side, with academy and reserve team players such as Andrea Pereira and 18-year-old Tahith Chong making up the rest of the starting XI.
Despite United's on-paper superiority, they were left frustrated at their inability to break down a stubborn San Jose side.
AC Milan Lineup
Gattuso arguably has a more experienced crop of players to pick from during this tour, though will hope to rotate as many in his squad as possible.
Fabio Borini and Suso will push for starts after featuring in last week's win over Novara, whilst Ignazio Abate may get a start in his customary fullback role.
Manchester United Lineup
The depth of established senior players in Mourinho's player pool is shallow, though the youth in his squad will enjoy the opportunity.
Mourinho has stressed that those who were featuring heavily in the World Cup will be likely to miss the start of the season, meaning their involvement in United's pre-season may be limited.
Key Battle: Riccardo Montolivo (AC Milan) vs Scott McTominay (Manchester United)
The midfield battleground will pit youth against experience as veteran Riccardo Montolivo may well line up opposite United youngster Scott McTominay in the central areas.
Montolivo, now 33, has had an illustrious career in the holding midfield role, and with both sides likely to line up in similar styles, the Italian will look to control proceedings against the comparatively inexperienced Scot.
Both players featured only in the second period of their previous respective games, so should be fresh and ready for a start.
Mourinho was frequently public in his praise for McTominay last season, and the 21-year-old will look to build confidence heading into a pivotal season.
Mourinho's men to step things up?
He may not have a full-strength, first-choice squad at his disposal, but Mourinho won't be over the moon having seen his side fail to win either of their opening two matches on their five-game tour.
Milan will represent a different test for the United youngsters, and the Portuguese must decide whether to give his youth a chance against a more solid opponent, or elect a more experienced set of players in search of their first pre-season win.
The absence of those who played in Russia will be a boost to the younger players looking to make a breakthrough, but will they take their chances?
Players to look out for
Milan forward Patrick Cutrone has been around the Italian side for some time, flirting with the first-team. At 20 years of age, Cutrone will hope to make the 2018/19 season his breakthrough one, and a positive pre-season will give him the platform he needs.
United midfielder McTominay and defender Axel Tuanzebe are now 21 and 20, respectively. Both have been in and around the fringes of the first team for some time at Old Trafford, though the pair must now wonder if time and chances will run out for them in Manchester.
This pre-season will be important for the duo, but can they give the manager a problem come early August?
Prediction: AC Milan 2-1 Manchester United
Pre-season friendlies aren't the easiest fixtures to predict, though the Italians may fancy their chances with a near full-strength to choose from.
Mourinho will be quietly eager for his side to register a win and get the tour off and running, though the weakness in depth may be a factor for his side as the game wears on.
Gattuso's side will be the fresher of the two having only played the one friendly to their opponents' two, and the Italian is keen for his players to become settled in his style of play quickly. 2-1.