On a night when they signed Ryan Lowe, Sheffield Wednesday were knocked out of the Johnstone's Paint Trophy on penalties by Bradford, while his former club, Bury, were also eliminated on spot-kicks.
Sheffield United left it late at Burton, Scunthorpe progressed at the expense of Hartlepool, Huddersfield beat Northampton, Walsall defeated Shrewsbury, and Tranmere needed penalties to see off Port Vale.
Lowe's six-figure-fee move to Gary Megson's Wednesday was confirmed on Tuesday night, but he will have had to watch his new club lose on penalties to Bradford after a 0-0 draw in normal time at Valley Parade.
Bury's disappointment at losing star man Lowe was compounded, as they were also knocked out on spot-kicks by Crewe after 90 minutes of stalemate.
A second-half brace from in-form striker Bobby Grant earned Scunthorpe a 2-0 victory against Hartlepool.
Tranmere progressed to the second round after a penalty shoot-out win over Port Vale following a 1-1 draw after 90 minutes.
Danny Wilson's Sheffield United continued their positive start to the season, as they came from a goal down in the final 14 minutes to win 2-1 at Burton.
Lee Novak was again Huddersfield's hero, as he struck an 82nd minute winner to secure a 2-1 victory at Northampton.
Walsall survived Andy Butler's own-goal to knockout Shrewsbury, with a 2-1 win coming courtesy of Ryan Jarvis and Richard Taundry.