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All the information here is from the Guardian Unlimited’s excellent ‘The Knowledge’. See ‘The Knowledge’ for thousands of fascinating bits of football trivia:
http://football.guardian.co.uk/theknowledge/
Manchester United’s Denis Law became the first player ever to miss in a penalty shoot-out in the semi-final of the Watney Mann Invitation Cup against Hull on 01 August 1970. Ian McKechnie was the goalkeeper. Later that year the penalty shoot-out was adopted by UEFA and FIFA.
The world record for the most penalties being taken in a shootout occurred in the 1988-89 Argentine Championship, where penalties were taken after drawn matches for an extra point. In the match on November 20 1988 between Argentinos Juniors and Racing Club, which had finished 2-2, 44 penalties were taken before Argentinos emerged as 20-19 victors.
The European record for the most penalties being taken in a shootout occurred in a match between Genclerbirligi and Galatasaray on November 28 1996 in the Turkish FA Cup Genclerbirligi eventually won the penalty shoot-out 17-16. Of the 34 penalties taken, only one was missed.
Bayer Leverkusen keeper Jorg Butt scored and saved a penalty in Hamburg's 3-1 victory over Schalke in the 1999-2000 season.
Former Paraguayan captain Jose Luis Chilavert scored and saved a penalty in Velez Sarsfield's 2-0 win over Independiente in 1999.
Chilavert also became the first goalkeeper to score three penalties during Velez Sarsfield's 6-1 victory over Ferro Carril Oeste in November 1999.
Cruzeiro striker Alex (now of Fenerbahce) can lay claim to an even more spectacular record: during the final-round Brazilian Championship clash at Bahia in December 2003 he scored four times from the spot - all in the first 37 minutes.
Argentine striker Martín Palermo is in the Guinness Book Of Records for missing the most penalties in a game. In July 1999, during the 3-0 Copa America defeat against Colombia, Palermo conspired to miss three spot-kicks.
In 1988 there were no draws in the Brazilian league, as every tied match would be followed by a penalty shoot-out with the winner taking two points (rather than the customary three) and the loser one point. In a match against Flamengo, Palmeiras lost their goalkeeper Zetti with a broken leg at the very end of the second half. Centre-forward Gaucho was thus placed in goal and heroically saved two penalties in the shootout to give his team a historic triumph.
Botswana goalkeeper and captain Modiri Marumo was sent off during a Castle Cup shootout against Malawi in May 2003. Having been booked for time-wasting before Malawi scored their third spot-kick, Marumo "reacted to a pat on the shoulder from opposite number Philip Nyasulu by punching him in the face and got a red card".
The first recorded example of a ‘two-man penalty’ occurred on June 5, 1957. Belgium entertained Iceland in a World Cup qualifying tie. Already leading 6-1, Belgium were awarded a 44th-minute penalty. Up stepped Rik Coppens to take it, but instead of firing towards Björgvin Hermannsson in the Iceland goal, Coppens nonchalantly passed to team-mate André Piters, who returned the favour, enabling the former to score past a stunned Hermannsson.
In the 2004 African Champions League final Enyimba FC of Nigeria and Tunisian side Etoile Sahel went to penalties after the two-legged tie finished 3-3, and the former opted to switch keepers. Off came Vincent Enyeama, with penalty specialist Dele Aiyenugba taking his place. Aiyenugba duly saved Ben Frej's effort as Enyimba prevailed 5-3 and retained their crown. Incredibly, Enyimba had done exactly the same thing in the semi-finals against another Tunisian side, Esperance, where Aiyenugba saved two penalties and saw two others missed.
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