Having achieved the win as a player Howley is now determined to savour that same victorious thrill as a coach.
Now the RBS 6 Nations tournament is over, he knows there will be little respite as that crucial date of June 5 will appear as a landmark opportunity in his rugby diary.
Yet again Wales will be facing the current World Cup champions and everyone knows that South Africa step onto every field of play with a winning mentality.
Howley's memories of June 1999, at a time when Graham Henry's Wales were half way through a 10 match unbeaten run are vivid.
"In the first 20 minutes we were as good as we had been all year and if we had taken our chances we could have been out of sight by half time," he said.
In the second half the Springboks emerged from the tunnel a different side and fully tested the Welsh defence.
Howley said: "There were 15 minutes of intense pressure yet the boys fought fire with fire. Having survived the onslaught we pulled ourselves together and went on to win the game 29-19 with Jenks finishing with another 19 points. It was an awesome feeling."
Wales had beaten South Africa and, to date, for the only time. Now as assistant coach of Wales Howley knows that the challenge is just as tough for the players of today - but so is the determination to win.
The encounter takes place just before the Wales squad fly out to play against New Zealand in a two Test summer tour.
June will be a month of brutal rugby encounters for Wales as Warren Gatland's squad starts the build up to the autumn of 2011 when the world title will be the prize.
Howley explained: "We're on the road to the Rugby World Cup and it's a great incentive to play South Africa in your own backyard. Whatever has been said about which players will or will not travel to Wales in June, any team that represents South Africa will be extremely tough to beat.
"You hast have to look at the squad they brought over in the autumn. They even had a reserve side that played in midweek against the likes of Leicester and Saracens. Physically South Africa are always a huge challenge.
"It's also an opportunity for us to select players who can put their hands up for selection for inclusion in the side as we approach the Rugby World Cup itself.
"Looking back at the win over the Springboks in 1999 it is disappointing that we haven't beaten them again in the decade since that game. We had a missed opportunity in the autumn of 2008 and again during last summer with the Lions so whether as a player or a coach it's great to have the opportunity to put that right come June."
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