The 22-year-old, who spent seven months on loan at Ainslie Park last season where he scored eight goals, has joined on a one-year deal from Falkirk.
The player went straight into the squad for last night’s second match-up with their SPFL League Two rivals in just ten days – City having beaten the Coatbridge-based club 4-0 in their league curtain raiser.
Despite trailing to John Cunningham’s first-half opener, City rallied after the half-time interval and it was that man Shepherd who found the back of the net with a well-deserved equaliser.
Blair Henderson, who had netted a hat-trick in the previous win over Rovers, was at it again as he put the hosts ahead for the first time in the tie with 13 minutes remaining.
Henderson made sure of City’s passage into the next round when he notched his second from the penalty spot following a foul by Rovers goalkeeper Daniel Potts.
“Having had such a positive impact last season it’s great to finally capture Scott on a permanent contract,” City boss James McDonaugh said of landing Shepherd.
“I’ve been working on this signing for a long time and I’m sure that it is one which everyone connected with the club will be happy with.”
City return to league duty against Stirling Albion on Saturday.