Strachan has moved into fifth place based on wins and draws divided by games played but Hendry reckons Brown, pictured right, might just be the best of all time given his record of leading Scotland to two major tournaments and coming so close to a third.
However, he desperately hopes that Strachan can take the next step and qualify for the 2018 World Cup so that he can lose the title as the last man to skipper the side on the big stage.
Hendry, who played for Strachan at Coventry City, said: “It may be statistically accurate to say that Gordon has gone ahead of Craig but it just shows you that statistics don’t paint an accurate picture.
“Craig took us to two major tournaments back to back and was so close to making it three in a row when we narrowly lost out to England in the Euro 2000 play-offs.
“There is a good argument to say that he has been the best Scotland manager we’ve had, so Gordon has got some work to do to emulate his achievements but I hope he can.
“Don’t get me wrong, Craig had his critics because we played in a certain way that some people didn’t like. We were set out in way that we were hard to beat, but also with the ability to create and take chances.
“If we took a chance to go ahead in a game then we were going to make sure that the opposition didn’t get back into it.
“Keeping clean sheets was our platform but you obviously have to go and win games to qualify for tournaments and that’s what we did by getting to Euro 96 and World Cup 98.
“I don’t think there is any doubt that Craig’s achievements were not given as much credit as they deserved at the time.
“But if you look at it now, his record is looking better and better.
“The team back then had players competing at the highest level. We had players at the top of the English Premier League and some who had won it. Paul Lambert who had just played in a Champions League final, John Collins who was in Monaco and Rangers and Celtic players were playing in Europe every season.
“We just don’t have that right now. How many are playing every week in the Premier League?
“I couldn’t even tell you who our highest-ranked player is – maybe Andy Robertson at Liverpool but he’s not a regular.”
Hendry is still fiercely passionate about his country and reckons that Strachan can deliver by beating Slovakia on Thursday and then Slovenia on Sunday.
He said: “It’s black and white for us. We need to win the two games which will give us second place and we will see who we get in the play-off.
“I’m pleased for Gordon. Although I didn’t have a great time at Coventry for whatever reason I had total respect for Gordon and I always got on well with him.
“I’m glad for him that we do have a chance going into these final two group games, even if we did have to get a little bit of help from England in terms of beating Slovakia.
“Listen, we didn’t beat the best of nations in Malta and Lithuania but the point is we have given ourselves a chance. It’s up to Gordon to send out a team to beat Slovakia and then that’s 50 per cent of the job done and we get ready for Slovenia.
“The thing is, they could be out of it by then if they lose to England at Wembley so I’m not sure if that’s good or bad for us.
“I can’t imagine they would roll over but if they have nothing to play for some players might switch off.
“If Gordon does win these two matches and then goes on to succeed in the play-off you would have to say it would be something very special.
“I never thought I would be the last Scotland captain to lead out the country at a major tournament.
“It’s frightening that it’s 20 years since we’ve done it. Will it change? Let’s hope so.”