Missing from last year's swim, Sheppard returned in fine style to take out the Men's Open section of the event in 18:42 in what he described as the toughest conditions he could remember in his many years of competing here.
"I've done maybe 12 or 13 of these and this would have been the toughest one and you can probably see that with the time. The tide had turned and it became really choppy and I just slogged the whole way," Sheppard said.
Super mum Naantalie Marshall also walked away with another winner's medal in the Open Women's section in a time of 22.00 - just one second ahead of teenage Point Lonsdale surf life saver Annaballe McPhail.
The 41 year old mother of two believed it was around the twentieth time she had contested the swim and had not kept a tally of how many wins she had notched up in Open and age categories.
Rough seas prompted her to ring ahead before leaving Anglesea to double check the race was still on.
"It was really really challenging so congratulation to everyone who finished the event, she said. It's very choppy and we're lucky it's a little protected. They always run a very good event here and they make everybody feel very safe.
"For some reason this swim felt like it went on for a very long time."
"It's really nice to see girls like Annabelle coming through. We've had girld that have been doing quite well int heir twenties,..but to have a 17 year old coming through is really good and I hope she can continue for a long time," Marshall said.
Earlier in the day future stars Matt Gilling and McPhail won the male and female sections of the 3.8km swim. Like McPhail, Gilling backed up for the Open 1.4km swim, also finishing second by the narrowest of margins.
Organisers were forced to move start and finish lines some 300 metres, because of a lack of sand and exposed rocks on Point Lonsdale's front beach.