There are fans on social media who even remember him playing for Bidvest Wits, which used to be called Wits University back then.
He then moved to England to play for Manchester United for nearly a decade, making 294 appearances. Bailey also represented England on two occasions.
Younger football fans in South Africa would be more familiar with Bailey as a television anchor and presenter on SuperSport television for many years.
He married a Namibian beauty queen and former Miss Universe Michelle McLean and left the country for the United States, where he is working for BeIN Sports TV. There are some South African fans asking Bailey to return to SuperSport.
South Africans fans hardly hear of Bailey's whereabouts in recent times because he is out of South Africa's television limelight, but he got their attention by making a number of Tweets about David de Gea's contract extension at United.
Bailey wanted to compare his salary to De Gea's at the same age, and at the same club. The former Kaizer Chiefs keeper also went on to back the Spaniard, saying his best form has returned in the Premier League.
You can read Bailey's Tweets and the responses from South African fans below.
Delighted they DeGea has signed a new contract for us ...he’s back to his best form and will be a crucial part of a successful team https://t.co/RBIczMo9i1— Gary Bailey (@gary_bailey1) September 16, 2019
Delighted that DeGea has committed to staying at United ... at same age and number of appearances, I was on $400 per week ... he will be on $400 000 per week ...I’m not jealous at all 😂😂😂— Gary Bailey (@gary_bailey1) September 16, 2019
David De Gea @D_DeGea is just a few appearances from overtaking @gary_bailey1 (who is on 375) and therefore becoming the longest serving Manchester United player to never score a goal for the club. (@Pschmeichel1 scored one and @AlexStepney1 scored two)— Wayne Barton (@WayneSBarton) September 16, 2019
Miss you on Supersport— #AM9 (@missp000) September 17, 2019
We miss you Gary come back to SuperSport😭— #MUFC 🔴 (@posyworldwide) September 17, 2019
Remember watching you play for Wits University, can’t believe that was over 40 yrs ago— Aliwell North (@aliwell_north) September 17, 2019
Why on earth did they pay you in dollars?— Michael Hinkin (@MikeyH2K7) September 17, 2019
You were the best Gary 💪💪💪— Weskido West® (@Weskido) September 17, 2019