International call-ups have denied Middlesbrough the services of Kris Boyd, Stephen McManus, Barry Robson, Kevin Thomson and Tarmo Kink.
Willo Flood faces a lengthy lay-off after dislocating his knee against Ipswich on Saturday, while Gary O'Neil is also sidelined.
MATCH FACTS
Head-to-head
• This is a repeat of the memorable 1997 FA Cup semi-final, when the sides shared six goals after extra time at Old Trafford. Middlesbrough won the replay 3-0 at Hillsborough.
• Middlesbrough won the last League Cup meeting between the clubs, in 1999. It was the second time they had been drawn together in the competition: in 1983, Chesterfield progressed to the second round after a penalty shoot-out.
• Boro have won half of the 20 competitive meetings between these clubs, with Chesterfield winning six times.
Have your say on the game
Chesterfield
• Chesterfield have only won one of their last seven first-round ties in this tournament.
• In 2006/07, they matched their best ever performance by reaching the fourth round: knocking out Wolves, Manchester City and West Ham before losing on penalties to Charlton. All those matches were staged at their Saltergate ground.
• This is the fifth season in a row they have been drawn against a Championship club in the first round.
• This will be Chesterfield's first cup tie in their new home at the b2net Stadium.
• Manager John Sheridan scored the winning goal for Sheffield Wednesday against Manchester United in the 1991 League Cup final.
Middlesbrough
• Middlesbrough are appearing in the first round of the League Cup for the first time since 1990.
• Their League Cup final victory over Bolton in 2004 is still the only major piece of silverware the club has won in its 134-year existence.
• They were last humbled by lower-league opposition in the competition in 2006/07, losing to League Two Notts County.
• Boro have won only one of their last nine away games.
Source: BBC Sport
Source: BBC Sport