#4 Ole Gunnar Solskjaer
Manchester United’s caretaker boss made 235 EPL appearances for the club he now manages, scoring 91 EPL goals in total and winning the league 6 times. But "The Baby-faced Assassin" could never find the net at Anfield, neither in the Premier League nor in any other competition.
Interestingly, during his last stint as a Premier League manager with Cardiff City in 2014, he faced a Liverpool side bang in the title race. After the game, which Liverpool won 6-3, when asked about Liverpool's title challenge, he said: "I couldn't care less."
In two weeks, he will face a Liverpool side in midst of a title challenge again. If Liverpool do win, he can expect a similar question again. Though as United's manager, he probably won't be able to give the same reply.