Reading have been involved in nine penalty shoot-outs. In the 1987-88 Simod Cup semi-final they beat Coventry 4-3 to reach Wembley for the first time; in the 1992-93 Associate Members' Cup they lost 2-4 to Exeter; in the 1997-98 FA Cup they beat Cardiff 4-3; in the 2001-02 League Cup they beat West Ham 6-5; in the 2002-03 FA Cup they lost 1-4 to Walsall; in the 2006-07 League Cup they beat Darlington 4-2; in the 2008-09 League Cup they lost 3-4 to Stoke; in the 2010-11 League Cup they lost 2-4 to Northampton; in the 2016-17 League Cup they beat MK Dons 4-2. The two winning shoot-outs against top division teams were as follows, players in red denoting a miss:
Coventry City Reading Kilchine 1-0 Curle Downs 2-1 Beavon Sedgely 2-2 Horrix Smith 3-3 Williams Bennett 3-4 Gilkes West Ham Utd Reading Hutchison 1-1 A.Smith Courtois 2-2 Murty Carrick 3-3 Rougier Sinclair 4-3 Harper Defoe 4-4 Igoe Dailly 5-5 Henderson Minto 5-6 Viveash
What I remember from the Coventry shoot-out was their main striker, David Speedie, bottling it and refusing to take a kick. The hero of the Cardiff shoot-out was keeper Nicky Hammond, who saved three shots.
Compared to this relative success in penalty shoot-outs, Reading have never won a tie on away goals. They lost to Colchester in 1983-84, to Derby in 1994-95 and to Bradford in 1999-2000, all in the League Cup.
In the 1999-2000 Associate Members' Cup, Reading beat Barnet 2-1 in sudden death extra time. Keith Scott scored the "golden goal".
In the 1989-90 Associate Members' Cup, Reading finished equal with Bristol City in their qualifying group. Top place, and a home tie in the next round, was decided on the toss of a coin, with the Robins calling it correctly.
Back in the days before penalty shoot-outs, Reading twice needed a third replay to decide cup ties. In the 1974-75 League Cup they beat Brighton, while in the 1989-90 FA Cup they beat Welling United.