Jamaica boss McClaren (left) is a former England manager while USA counterpart Pochettino has had spells in charge at Tottenham, Paris St-Germain and Chelsea
Steve McClaren's Jamaica were beaten 1-0 at home by a USA side managed by Mauricio Pochettino in the first leg of their Concacaf Nations League quarter-final.
Demarai Gray missed a penalty for Jamaica while team-mate Mason Holgate was sent off late on in Kingston.
An early goal for Ricardo Pepi proved enough to give the USA victory before the second leg in St Louis next week.
AC Milan attacking midfielder Christian Pulisic set up Pepi to score his 12th goal in 32 internationals with a shot which went in off the post early on.
Jamaica had the chance to equalise from the spot after USA keeper Matt Turner brought down Shamar Nicholson but former Everton winger Gray, who now plays for Saudi Pro League side Al-Ettifaq, was denied by an impressive save.
Holgate, who had an effort cleared off the line by Yunus Musah, was sent off after 86 minutes when he picked up a second yellow card.
The defeat - the first in five games for Jamaica under McClaren - gave Pochettino his first competitive victory after his first two games were a win and a loss in friendlies.
Elsewhere, Argentina were beaten 2-1 by Paraguay but remain top of the South American World Cup qualification group.
Lautaro Martinez put Argentina in front but a bicycle kick from Antonio Sanabria and an Omar Alderete header gave sixth-placed Paraguay victory.
Brazil forward Vinicius Junior missed a penalty for his side, who were held to a 1-1 draw by seventh-placed Venezuela.
A superb Raphinha free-kick gave Brazil the lead and, after Telasco Segovia equalised, Vinicius Junior had a spot-kick saved by keeper Rafael Romo.
Brazil are third in the group, in which the top six South American teams qualify automatically for the 2026 World Cup.
