Paul Hartley would love to clinch a hat-trick of William Hill Scottish Cup triumphs - but claims 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."
He added: "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."
Hartley will be praying on-form striker David Clarkson continues his hot streak until the Hoops clash on either February 7 or 8.
The former Motherwell striker made it eight goals in as many games with his stoppage-time winner against the Dons and his boss said: "David is in top form just now and long may it continue.
"Every time he goes on to the football pitch he feels like he's going to score. He's got great confidence just now.
"Did I expect this type of form from him when I bought him? I don't know. I knew he was quality and he had good experience it was just a matter of time of getting him fit. He's fitted in brilliantly and the goals have been terrific for him.
"Hopefully he'll continue this type of form but it's got to come to an end sometime."
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.
St Mirren overcame Spartans the last time the Edinburgh side reached the last 16, after a replay in 2006, but Spartans director David Bryce is hoping to go one stage further this time.
"We didn't get one of the big teams but we got a home draw against League Two opposition so we have a chance to get into the last eight, so I am happy with it," he said.
"We played Clyde then played Morton which is a step up and we did well, we won on merit.
"We are just happy to be in the draw, we deserve to be in the draw and to get a game we could win, so who knows what will happen next?
"But it is huge that we are in the last 16 again so to get through to the last eight would be magnificent for us, for all the work we put in at the club.
"We played Albion Rovers in the cup last year and they beat us 1-0 so I think we have a chance.
"It is not going to be easy but we proved on Saturday that we could handle bigger teams and it is a great advert for the Lowland League.
"I don't think either of their managers will relish coming down to Ainslie Park."
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