The former Manchester United winger numbers Kevin Keegan, Kenny Dalglish, Ruud Gullit and Graeme Souness among the managers for whom he has worked in a sometimes turbulent career, but readily speaks of Neil Warnock in the same breath as Sir Alex Ferguson.
"Neil is a colourful character who says what he thinks, but that's what I like about him," the 30-year-old Gillespie said. "Growing up at Manchester United was fantastic because Fergie was brilliant at nurturing young players - but I get on as well with Neil as I did with Sir Alex.
"He gives you praise when it is deserved but will criticise you when he feels it is necessary. He looks after his players and the team spirit here is great.
"He has been fantastic for me. I did not know what was going to happen after I was released by Leicester. It was a difficult summer, but Neil gave me a chance.
"I did not come here until the day before the new season, but he has shown faith in me by giving me a two-year contract. I didn't really get into the game today, but I'm fairly satisfied with my form so far and I know there is more to come.
"It is a relief to know I will not have the same uncertainty next summer and hopefully we will be spending it preparing for the Premier League."
The form of Warnock's side over the first third of the season suggests that to be the likely outcome, even though their eye for goal deserted them for the first time in 16 Championship games on Saturday.
The Cardiff goalkeeper, Neil Alexander, had to deal with only one shot of any note, while the Welshmen, beaten only once in 11 games since August, could have secured a win with better finishing after the fine passing of Jason Koumas created a number of chances.
Several times Warnock was moved to demand penalty kicks for suspected handball, but Dave Jones, the Cardiff manager, felt his side has just as strong a claim on official intervention.
"We had one in stoppage time that was clear-cut," Jones said. "But they had maybe one good shout as well. As for the rest, Neil can evidently see things I can't see so I'm going to try to pinch his glasses."
Sheffield United (4-4-2): Kenny; Kozluk (Geary, 54), Bromby, Morgan, Unsworth; Gillespie (Ifill, 63), Montgomery, Jagielka, Quinn; Kabba, Shipperley (Webber, 72). Substitutes not used: Tonge, Wright.
Cardiff City (4-4-2): Alexander; Weston, Purse, Loovens, Barker; Cooper, Whitley, Ledley, Koumas; Ricketts (Lee , 78), Jerome. Substitutes not used: Ardley, Parry, Margetson (gk).
Referee: C Foy (Merseyside).
Man of the match: Koumas.