Shanghai - Roger Federer saved an heroic match points as he fought for his life only to fall from the group stage for the first time in his career at the Masters Cup to end the season on a disheartening note on Friday.

Andy Murray's 4-6, 7-6 (7-3), 7-5 comeback win over the four-time champion lifted French debutant Gilles Simon into the weekend semi-finals along with the Scot.

Murray will play Nikolay Davydenko on Saturday while Simon faces Novak Djokovic.

Federer was twice treated for back pain in the dramatic third set, with the Swiss ending his 2009 campaign with a 15th loss. It took a shade over three hours for Murray to claim the nail-biting win.

The Swiss managed 11 aces in his losing effort, with 65 unforced errors while Murray was successful on six of 18 break point chances in the thriller which left Murray on a perfect 3-0 record in the Red group.

Federer had won four of the last five editions of the year-end spectacular, losing in 2005 to David Nalbandian and reaching the semis upon his debut in 2002 at Shanghai.

The Swiss claimed the first set and looked like clawing back from 2-5 in the second, saving a pair of Murray set points in the eighth game and breaking the Scot on a double-fault for 5-all.

Murray staggered into a tiebreaker where he squared the match a a set each before Federer called for the trainer to massage the back which had forced him to quit in Paris a fortnight ago.

Simon pounded alternate Radek Stepanek 6-1, 6-4 in 65 minutes, breaking three times and never in danger against the Czech who filled in at the last minute at mid-week for injured Andy Roddick.

Federer dropped the first of his three group matches to Simon, then subdued Stepanek while fighting a stomach virus to level at 1-1 and stay in the title hunt.

Federer now stands 27-5 at the season wrapup while Murray has qualified for the first time. (dpa)