At the US PGA Tour Qualifying School finals later that year Jeev missed out by a whisker from securing his card for 2003 courtesy a final round 77.

In year 2005, Jeev, by now a regular on the Japanese Tour came really close to winning his first title on that Tour. At the Okinawa Open Jeev enjoyed a four shot lead going into the final round but Kiyoshi Miyazato pulled the rug from under his feet and the Indian had to settle for tied second place.

Jeev MIlkha Singh’s moment of reckoning came in year 2006. Till that period he hadn’t won for seven years but this blot on Jeev’s CV was erased with a fantastic victory at the Volvo China Open. Jeev then topped it up with a win at the Volvo Masters, the European Tour's season-ending event, in Spain in October. On a roll, he went on to register back-to-back wins on the Japanese Tour at the Casio World Openand the Golf Nippon Series JT Cup. ON the Asain Tour, Jeev became the third Indian to win the Order of Merit title with a then record earnings of US$591,884. That year, Jeev also posted15 other top-10s on the Asian, Japan and European Tours. He made anbother appearance at the US Open in Winged Foot where he made the cut yet again. Jeev Milkha Singh was named the Players' Player of the Year and also won the Special Achievement Award in 2006.

In 2007, Jeev who played mostly in Europe and the United States played his first ever Masters – indeed the first ever time an Indian played the prestigious event too. Jeev made the cut once again finishing tied 37th. In fact there was a point when he actually led the field that week. Also played in all four rounds at the US Open, finishing 36th.

Year 2008 was yet another landmark year for Jeev Milkha Singh. The year began with second place finishes at the Indonesia Open and Ballantine's Championship in Korea, but a win at the Bank Austria Golf Open on the European Tour and Sega Sammy Cup in Japan set the ball rolling once again. Then came a win at the Barclays Singapore Open where Jeev got the better of golfers of the caliber of Padraig Harrington and Ernie Els by one stroke. A win here helped Jeev become the first man in Asian golf history to win over US$1 million during a season. He finished that season with the tally resting at US$1.45 million. IN Japan, Jeev registered a win at the Nippon Series JT Cup in Japan which saw him end the year in 35th place on the Official World Golf Ranking. Jeev also played his second Masters in 2008 where he made the cut for the second time in a row and ended the week at tied 25th place. He also became the first Indian to play the PGA Championship and actually finished ninth at the Major to record the best ever finish by an Indian in one of the four best golfing extravaganzas in the world. To top it all, Jeev was named Players' Player of the Year in 2008.

Jeev has had an average start to 2009 by his own standards. Making his third appearance at the Augusta Masters Jeev was drawn to play with none other than Tiger Woods. He actually out-drove Tiger on most of the holes but failed to make the cut for the first ever time in a Major.