Having won just once in seven encounters with this opposition, the German boss is priced at 19/20 (1.95) with dabblebet to leave America on a high with another win here.
The Red Devils ran out 3-1 winners when the sides previously met in the ICC back in 2014, and you can get odds of 12/5 (3.40) on them coming out on top once again.
However, four of the last five meetings between this pair have resulted in draws, and there are odds of 11/4 (3.75) available on them taking this one to penalties after another stalemate.
Sadio Mane, Mohammed Salah and Marko Grujic all made their first pre-season appearances in the victory over City, with Xherdan Shaqiri set to make his debut after joining up with the squad this week.
However, Nathaniel Clyne flew home on Thursday for family reasons.
Although he has complained about the lack of first team players available on the tour due to the World Cup, Jose Mourinho was able to call upon a fairly experienced line-up against Milan - including a strong defence.
A backline of Matteo Darmian, Chris Smalling, Eric Bailly, and Luke Shaw helped to restrict their opponents to a single goal, meaning they have conceded just twice in three games on the American tour.
With the ever-competitive Mourinho undoubtedly determined to ensure this game against familiar adversaries is more than a friendly, it seems likely that his side will dig in and defend once again.
Having ensured that six of the last seven encounters with Klopp's Liverpool have produced under 2.5 goals, odds of 23/20 (2.15) are well worth backing on United doing so once again in Ann Arbor.