The 52-year-old seems to think that the match at the iPro Stadium will be a close one and has suggested a 1-1 scoreline as the final result.
“I’ve changed my mind three times on this one!” Holloway wrote on Skysports.com. “It’s very difficult to call, so I’m going for a draw. They are both good teams, who will be up there at the end of the season.
“It’s going to take a little while for the Derby players to get used to Paul Clement. When they do click, they’ll hit a good run of form, they have got some undoubted quality there.
“If you offered Paul the 1-1 now, he would probably settle for that with the strength of Middlesbrough.”
Both Derby and Middlesbrough are aiming for a top-two finish in the Championship this season, which will secure them automatic promotion to the Premier League.
Hosts Derby will head into the encounter on the back of a 1-1 draw with Charlton Athletic at home.
The Rams have yet to win a competitive game this season, having drawn 0-0 with Bolton Wanderers away from home in their first Championship match of the campaign before losing the League Cup first-round tie to Portsmouth.
Visiting Middlesbrough have fared better than Derby so far this season, having played out a goalless draw with Preston North End away from home before defeating Bolton 3-0 at the Riverside Stadium on Saturday.
Aitor Karanka’s side have also progressed to the second round of the League Cup courtesy of 3-1 victory over Oldham Athletic away from home.