After defeating Aberdeen, the Easter Road side have been paired with Kilmarnock at Rugby Park in the last eight.
It is the third time this season that they have been drawn against a team they also faced in the competition last term, when they defeated Killie in the fifth round and Aberdeen in the semis before succumbing to a 5-1 defeat in the final against Hearts.
Fenlon hopes the omens are good for his side as he seeks a shot at Hampden redemption.
"That is three teams who we played at some point last year, which is unusual," he said.
"Hopefully it is a good omen, as long as it doesn't end the same way.
"We want to get to the final again, of course. It is something we are keen to do.
"We have a really tough quarter-final then another hard game, regardless of who it is, but our aim is to get back there, definitely."
Fenlon had a wonder strike from Gary Deegan and the brilliance of Ben Williams to thank for his side's last-eight place.
Goalkeeper Williams made six fine saves, most notably denying Scott Vernon from the penalty-spot – his fourth save from six penalties faced this term.
Deegan, meanwhile, scored his first-ever goal for the club with a spec-tacular 30-yard strike.
The midfielder has endured a traumatic campaign, having sat out over two months with a broken jaw.
"I have never seen Deegs strike a ball like that from distance," said Fenlon. "It was a fantas-tic goal. Gary has had a tough time over the last year so I am delighted for him."