The former Manchester United goalkeeper, twice an FA Cup winner in eight years at Old Trafford, relocated to South Africa after a terrible knee injury ended his career in England.
He is now the face of football on the country's sports tv channel SuperSport - the equivalent of Sky Sports in South Africa.
So who better to give an insight into just what the lads will face when they come up against current South African champions Orlando Pirates on July 26 and Kaizer Chiefs on July 29.
"People generally compare South African football to Division Two standard in England, maybe First Division for one or two teams," explained Gary.
"Orlando Pirates are certainly closer to Division One. But you will play them in their conditions - there will be a huge crowd, very, very partizan and it will be a typical pre-season or even like a cup tie where if you don't take it seriously, you could get nailed.
"They are a decent side who work hard for each other with a couple of national team players in Lesley Manyathela and Mbulelo Oldjohn Mabizela, both very useful.
"It won't be an easy game and a good pre-season test for Spurs.
"Kaizer Chiefs have one of the biggest official fanclubs in the world, people in South Africa believe in joining the club. Back in England, you would only do that if you are a serious supporter but here, anyone who believes in Kaizer Chiefs joins the fanclub and it is huge.
"That's is what they are talking about when they talk about having one of the biggest fan bases in the world.
"They will also have a very big, partizan home crowd in Cape Town.
"They are not quite as good as Pirates, not quite as solid, not quite as organised but they have a new coach in Ted Dumitru and he's had a fair amount of success in South Africa. It will be another good test and Tottenham will have to be professional.
"England showed the way against South Africa recently, if you put the effort in you can get away with a 2-1 victory but if you take it lightly and don't do the right things, you could get beaten."
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Gary Bailey has a simple warning for the lads before our trip to South Africa: Take the games lightly and you'll get nailed!