When Brendan Rodgers and Van Gaal meet in tonight's final of the International Champions Cup it will not be the first time that the pair have been in competition.
According to a Telegraph report, when Kenny Dalglish lost his job as Liverpool manager in 2012, Van Gaal was keen on being his replacement and he met with Ian Ayre to discuss the position.
Although Liverpool had already set their sights on Rodgers and had a different role in mind for the now United manager. The hierarchy at Liverpool regarded Rodgers as quite young and so wanted Van Gaal to take the role of director of football, and act as a mentor to Rodgers.
Liverpool's request was brushed off by both parties with Brendan Rodgers claiming he would not work under someone else, and Van Gaal not interested in being a mentor.
The Northern Irish manager reflected on the appointment process during a press conference ahead of Liverpool's first final meeting with United since the 2003 League Cup final.
He said: "It was obviously something before I came in. I’m not sure how many people the club spoke to. But for me coming in, I was always going to work with a team of people, rather than a director of football.
“I always think the manager is the technical director. He is the man who oversees the football development of the club, and I believe you should take on that responsibility when you are manager.
“He’s (Van Gaal) a very experienced manager, a very good manager and he’s gone into them, and he’ll make his mark.
“I’ve never met him before, but obviously I know of him through Jose, and I know he was very instrumental in mentoring Jose at Barcelona. I’m aware of the methods, I’m aware of how he works, and obviously he’s had a very good career."