Martyn Paterson (Central) two years ago and Graeme Lister (Pitreavie) last year were Simpson's first winners and both were unexpected triumphs.
Lister, in particular, produced unsuspected form to confound the few bookmakers left at this famous old professional 110 metres handicap.
A former half miler, he sped to the line in 11.62 seconds to capture the £4000 first prize from a start of 12.5metres.
His handicap has been cut by almost seven metres, making a repeat win seem unlikely. But Simpson expects last year's winner to "give them a fright".
Should he win through his heat, Lister may then face one of two 16-year-old Edinburgh AC members, Morro Bajo or Ben Robbins.
Bajo, a Gambian-born pupil at Drummond High, has been guided by veteran coach Bill Walker and was the third fastest senior in Scotland last season over 100 metres with a time of 10.76 secs and second fastest over 200 (21.77).
He also won the Gambian 100m title and could have represented Gambia in the Olympics, but rejected the chance, insisting: "I want to run for Scotland in the Commonwealth Games."
The Sprint backmarker off 3.5 metres, Bajo goes in heat seven where he faces a previous runner-up Gemma Nicol (Dunfermline, 16.5m)) and her mother Wendy (28.75m), both still bidding to become the event's first female winner.
Last year's New Year youth sprint winner, Robbins was a member of the Scottish under-18 rugby squad until he and his coach Dave Goodall agreed a year off for him to focus on his athletics.
He was the early 3-1 favourite with bookmaker Peter Collins after the draw.
Allan Hamilton is another young Edinburgh AC member who might surprise.A 20-year-old pharmacology student, he has little recent sprint form, although his record as a long jumper – he was runner-up in this year's national senior event – indicates he has the background to follow the example of another converted Edinburgh long jumper, the 1980 Olympic 100m champion Allan Wells.
Hamilton is coached by John Scott, whose other successes include World bobsleigh champion and Scottish long jump champion Gillian Cooke. He said: "Allan is an exceptional runner – he could do well and he wants the money."
The backmarker in heat eight off four metres, Hamilton has a trio of Jedforest runners to beat including Scot Richardson (7m). Also in his training group is another long jumper, Musselburgh native Sarah Warnock, who like Hamilton is studying at Queen Margaret and has a start of 20m in heat five where her rivals include previous runner-up Fiona Cleat (20,25m), two previous Sprint winners, Hawick's Leigh Marshall (5.75m) and Cumbie Bowers (Glenrothes 6.5m) and the strongest tip of the Border runners Dylan Ali (Tweedbank).