Not only will he come face-to-face with the coach of the Ticos' first World Cup campaign in 1990, but his team must also take on a familiar foe in the group stages.
Guimaraes was a member of the Costa Rican side that made an impressive debut in Italy 12 years ago by reaching the second round.
Their coach at the time was wily Serb Bora Milutinovic, who is now at the helm of World Cup newcomers China.
It's an honour to play against one of my teachers who now coaches China
It will, no doubt, be a strange feeling for Guimaraes when he is reunited with Milutinovic as the Ticos play China in their opening group game on 4 June.
But Guima, as he is popularly known in Costa Rica, seems to be looking forward to it.
"It's an honour to play against one of my teachers who now coaches China," said Guimaraes when the draw was made last year.
Both men have fond memories of Costa Rica's last outing at the World Cup.
Despite losing to Brazil, the little Central American side surprised the pundits by beating Scotland and Sweden to secure a place in the last 16.
Their World Cup adventure finally came to an end with a 4-1 defeat to Czechoslovakia, but by then, they had earned the respect of their peers.
Costa Rica face another ghost from the past in the form of Brazil in their final group match on 13 June.
Although some people may claim that they did well to hold the South American giants down to a 1-0 win in 1990, many agree that Brazil's goal was a touch fortunate.
In the 33rd minute, Mozer of Brazil headed on a throw-in from the right side, the ball glanced off the elbow of Costa Rican stopper Montero and another Brazilian, Muller, was able to score.
When they meet again in Suwon, Brazilian-born Guimaraes will, no doubt, be relishing the chance to even the scores.