His 2015 Spireites side were defeated to Preston in the League One semi-finals and his Pompey team lost to Plymouth the following year at the same stage of the competition.
On Tuesday night he leads his Chesterfield players into battle against Halifax in the National League play-off elimination round.
“I have been lucky enough to be in play-off situations, one obviously here with Chesterfield against Preston and one with Portsmouth against Plymouth,” Cook said.
“They are exciting, there are big attendances, they are 90mph football, I think Steve Cooper from Nottingham Forest said that everything goes out of the window, I think that is probably the right case, so we will prepare our players the best we can for what situations arise.
“I have been lucky enough to sample some great days in football, going up in the play-offs is not one of the things that I have ever sampled so it is something that I crave for as a manager as well.”
Hosts Halifax will be hot favourites for the clash and Cook has nothing but praise for the job Pete Wild has done at the Shaymen.
He said: "They have got a manager who I have got to know since I have come back to Chesterfield and I have got a lot of respect for him and his club. I think they are an outstanding club who are fighting at the top end of the league where there are some bigger teams, without a shadow of a doubt.
“Halifax are a very, very strong side. They have got great qualities within the team and we know we are in for a really difficult night.
“With Halifax what you see is what you get. I don’t think in football you can underestimate levels of organisation, honesty, worth ethic, team spirit and belief. And the most important bit to cap it all - having good players with an appetite to work, I think that is the key to football.
“Pete has assembled a really, really good squad which is full of those qualities. They are a really good side, they are a really hard side to beat, the goals against and clean sheets is a fantastic achievement for any team.
“We know we are in for a difficult night.”