Former Chelsea winger Duff, 45, won back-to-back Premier League titles under Mourinho during his time at Stamford Bridge.
Damien called Jose Mourinho after Shelbourne's League of Ireland title triumph
Duff joked Mourinho had called but he was actually left hanging by his old boss
Nearly two decades on and Duff claimed his first title in management in thrilling fashion on Friday night.
Shelbourne led Shamrock Rovers by two points heading into their final game away at Derry City.
And a 1-0 win was enough to clinch the League of Ireland for Duff's men - the club's first title since 2006.
During the post-match celebrations in the dressing room, Duff, 45, pledged €500 (£420) to the party if ex-boss Mourinho did not pick up the phone to him.
The old Newcastle and Fulham man put it on speaker and let it ring as he and his players nervously awaited a response.
Awkwardly, Fenerbahce head coach Mourinho failed to pick up - with Duff pretending to have gotten an answer before putting his phone away.
While waiting, he also joked he would go "double or quits on the next one".
Duff, who has been manager of the Irish club since 2021, revealed following Shelbourne's title win that Mourinho had sent his players a message in the lead-up to the game.
He said: "Why Jose?' Because do I try and build, have we tried to build a siege mentality, us against the world like he did? Absolutely.
"It would be mad not to tap into him. So Monday, Tuesday, Wednesday, Thursday, there was posts on the Instagram page. Powerful lyrics, powerful words that would resonate and have a meaning to tie in for tonight.
"Then, in the team meeting, there was a private message from Jose speaking about what it takes to win a title as a team, as an individual.
"It blew the guys away. A video that was shown in the Everglades two hours before the game."
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