The Dark Blues of Dundee get off to a shaky start but finally see off a spirited Raith Rovers side.
The Dark Blues new signing Sofian Moussa comes off the bench to open the scoring, before Hendry scored a dramatic late winner in injury time to secure all three points in the first round of the Betfred Cup.
Paul Hartley was the man who brought McPake to Dens Park in the summer of 2014 as he prepared the Dee for their Premiership arrival but now, he will face off against his old gaffer as Dundee hope to build on Saturdays 3-0 victory over Raith Rovers.
Despite now being managerial rivals, McPake is thankful that recently appointed Cove Rangers boss Hartley helped him get started on the road with coaching.
“I liked the way he worked. He was unfortunate here, I think," said McPake.
“The second season we finished seventh in the league and we were probably better than what we were the season before when we finished sixth. He had us going well here and it was unfortunate the way it ended, but he’s someone I really liked.
“I was grateful. He was the one who got me into coaching. Well, not got me in, but gave me a head start. If Paul hadn’t done that then I wouldn’t be sitting here, that’s for sure. Knowing Paul, he wants to work and he takes on projects.
“He’ll want to get them up through the leagues. That’s what will motivate him. He’s a hard worker and he will do well there.”