Paul Hartley would love to clinch a hat-trick of William Hill Scottish Cup triumphs - but claims that landing the trophy as Dundee boss would be his sweetest victory yet.
The Dens Park manager won the competition twice as a player - first with Hearts in 2006 and then again with Celtic three years later.
But the former Scotland midfielder will have to negotiate a way past the Hoops if he is to taste another Hampden party after the Dee were handed a home tie with Ronny Deila's men in the draw for the last 16.
Hartley - whose side knocked out Aberdeen in Saturday's fourth-round clash - said: "Winning the cup as a manager would mean more that doing it as a player.
"Management is totally different from playing.
"You are looking after a group of players and you are looking for a bit of success.
"It's a tough draw. It's doesn't come any tougher than Celtic but we're at home and that gives us a good chance.
"Whether it's the first round or the final you have to beat the top teams to win.
"The game is another two months away and hopefully our form is good up until then," he added.
While Dundee host the Hoops, there is another all-Scottish Premiership tie, with Partick set to take on the winner of Tuesday's replay between Inverness and St Mirren at Firhill.
Holders St Johnstone have been handed a trip to Dumfries after drawing Queen of the South, while Rangers will meet Raith Rovers at Ibrox.
Hibernian host Arbroath, while Annan or Brechin will travel to Falkirk. The victor of Stranraer's replay with Dunfermline will progress to a home clash with last year's beaten finalists Dundee United.
But the fairytale element to this year's contest continues.
After beating League Two side Clyde and League One leaders Morton in the previous rounds, Lowland League side Spartans have been handed another home draw against the winners of the Berwick Rangers versus Albion Rovers replay.