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Player-captain Montgomerie pitted himself against 18-year-old Ishikawa, widely tipped as a future number one, in the opening alternate-shot foursomes match and the gamble misfired spectacularly.
Europe were trailing in three games and up in just one before a great comeback by Peter Hanson and Soren Kjeldsen earned them a half point against the Indian duo of Jeev Milkha Singh and Gaganjeet Bhullar.
Asia stunned Europe with a 10-6 victory last year and Montgomerie is looking to avenge that defeat as a confidence-booster ahead of the Ryder Cup against the United States in October.
"I am delighted with the way we escaped. At one stage we were three to one down and it is a big difference to be behind two and a half to one and a half," said Montgomerie.
"All credit to the players from coming back especially Peter Hanson and Soren Kjeldsen for getting a half point from their game.
"We need to fight back and win the (four ball) series tomorrow to get on equal terms going into the singles."
Asian captain Naomichi "Joe" Ozaki, who led the team to victory last year after losses in the first two editions, was pleased to be ahead by a point.
"I would have been happy with 2-2 so I am delighted to be leading by one point at the end of the day," he said.
The 46-year-old Montgomerie and partner Pablo Martin of Spain made a brilliant start by winning the first two holes but world number 30 Ishikawa and countryman Koumei Oda reeled off four birdies in eight holes to take control.
Back-to-back birdies at the island-green eighth and the ninth, where Ishikawa chipped in from 25 yards, were key to the victory at Amata Spring Country Club.
The Japanese duo wrapped up the contest 3 and 2 with an unlikely halve at the 16th where Ishikawa lost a ball in the bushes.
"I was not looking to chip it in at the ninth but it turned out to be very good for the team especially after the birdie at the eighth," said Ishikawa, who became the youngest winner of the Japan Tour moneylist after four wins last season.
Thai duo Thongchai Jaidee and Prayad Marksaeng, who had a 100 per cent record last year, grabbed the second point for Asia with a scrappy 3 and 1 victory over world number seven Henrik Stenson and England's Simon Dyson.
The local heroes managed just three birdies but were never behind as Swedish big gun Stenson and Dyson carded six bogeys against a solitary birdie in a ragged round.
The Swedish duo of Robert Karlsson and Alexander Noren gave Europe a much-needed point with a thumping 4 and 2 victory over Liang Wen-chong of China and Korea's Charlie Wi.
The Danish-Swedish combination of Kjeldsen and Hanson clawed back from two holes down with five to play for a fighting halve with Singh and Bhullar.
They came close to a win with former Asian number one Singh holing a tricky putt on the last for the half point.
The Royal Trophy continues with four ball matches on Saturday and singles on Sunday.
