Martín Palermo owns some of the happiest memories for Boca Juniors fans; however, he also holds one of the most infamous records in Copa América history and, of course, for the Argentine national team, having missed three penalties in a single match.

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Palermo arrived at the big stage as the main striker for an Argentine team filled with Boca Juniors players, displaying sensational form that left little to the imagination of what was to come. It was on July 4, 1999, when Colombia staged one of the most memorable victories in Copa América history, defeating Argentina 3-0, while Palermo missed all three penalties awarded to the albiceleste.

The chronicle unfolds as follows: Palermo's first miss occurred after Ernesto Filipini converted a penalty following a handball in the box. Palermo took charge of the penalty but hit the crossbar.

The second miss by Palermo was nearly identical to the first, as the talented Argentine striker sought redemption but once again sent the ball over the crossbar.

The third miss by Palermo seemed like fate playing a cruel joke, as after a foul by the legendary Iván Ramiro on Palermo, he had another chance to erase his dismal performance. This time, however, Migue Calero stepped up to save the shot and prevent another goal from going past him.

Colombia delivered a historic performance with a 3-0 victory over Argentina, while Martín Palermo endured a very bleak night that etched his name into the Guinness World Records.