The Reds who were defeated by League One Crewe in the first round last season will head to League Two Lincoln on either Tuesday 11th August or Wednesday 12th August.
This is the fourth time the two sides have been paired together in the League Cup with the most recent encounter being in a two legged affair in the 1999-2000 season. Barnsley won 4-2 in the first leg at Lincoln and then drew 2-2 at Oakwell. Neil Shipperley, Robin Van Der Laan (2) and Nicky Eaden scored the first leg goals and Mike Sheron and Eaden netted in the second leg.
They were paired together again in 1979-80 in another two legged encounter with both teams winning their home leg 2-1 and Lincoln triumphed on penalties at Oakwell.
The only other one legged meeting was at Oakwell in 1964 when The Reds won 2-1.
The two sides haven't met in league combat since the 1975-76 season.
In terms of League Cup success, neither side has ever won the trophy since it was created in 1961. The furthest Barnsley have got is a Quarter-Final replay with Liverpool in 1983 which they lost 3-1 whilst the furthest Lincoln have progressed is the fourth round in 1967-68 where they lost in a replay to Derby County.
Last year The Reds were humbled 2-0 at Crewe whilst Lincoln also exited in the first round- 3-1 at Derby after extra time.
Barnsley League Cup history:
Played: 134 Won: 45 Drawn: 31 Lost: 58 For: 182 Against: 197
Lincoln League Cup history:
Played: 129 Won: 41 Drawn: 32 Lost: 56 For: 189 Against: 218