The Newcastle manager featured in some important ties during a glittering playing career, including a Euro 96 semi-final and two FA Cup finals.
But he knows the significance of Monday's game against Portsmouth towards the Magpies' hopes of staying up.
He also believes Newcastle need to win their other two home clashes against Middlesbrough and Fulham if they are to retain their top-flight status.
He said: "It's my biggest game for a long, long time. We all know the stakes, so we need to go out and get three points.
Importance"It sounds easy, but it won't be. We all know the importance of it. Now we just need to go out and do it. We have to go at it and grab those three points.
"I think nine points could just be enough, looking other teams' fixtures.
"I might be wrong, but I'm asking the players to win their three home games, starting with Monday against Portsmouth."
Shearer has happy memories of playing Portsmouth as he finally beat Jackie Milburn's record of 200 goals for Newcastle in a 2-0 victory over Pompey on 4th February 2006.
"I hope it is an omen to clutch on to," he said. "But what I am aiming for is my first win as a manager."
Gutierrez viewWinger Jonas Gutierrez is also in no doubt as to the task at hand.
"This is going to be my most important game for the club," he said.
"We know exactly where we are so we must take three points.
"The training has been very good and everybody is prepared for the game with Portsmouth.
"All the players are aware of just how serious this situation is."