Sam Byram and Chris Wood missed penalties as 10-man Leeds United bowed out in the first round of the League Cup to Doncaster Rovers at the Keepmoat Stadium on Thursday.
Championship side Leeds had beaten Rovers twice in the competition over the previous four years but, after Andy Williams cancelled out Lewis Cook's opener, it was the hosts who progressed on penalties.
Youngster Cook was sent off for a poor challenge in the first half to make life difficult for Leeds, whose shootout defeat saw them exit the League Cup at the first-round stage for the first time.
Cook gave Leeds an advantage with his maiden senior goal 14 minutes in - tapping home after Mirco Antenucci's effort was parried by Thorsten Stuckmann.
However, the home side were level through Williams after Scott Wootton clattered into Cedric Evina, referee Keith Hill given no option but to point to the spot.
Hill remained in the thick of things as he showed Cook a straight red for a two-footed lunge on Aaron Taylor-Sinclair.
The second period failed to live up to the excitement of the first - substitute Wood seeing penalty appeals waved away amid grappling in the box.
After extra-time had finished goalless, Byram and Wood both skied penalties, the latter doing so in spectacular fashion, allowing Richie Wellens to convert the winning spot-kick.
Doncaster face Ipswich Town at home in the next round.
