| Fernando Alonso led a McLaren one-two in the opening practice session for the Monaco Grand Prix, while the Ferraris only managed fifth and eighth.
Hamilton was the early pacesetter, his 1:18.686 effort after 23 minutes being 1.5 seconds quicker than teammate Alonso's first flying lap.
That gap was soon cut to 0.4 seconds when the session resumed following a brief red flag while Christijan Albers' Spyker which retrieved from Tabac, where it had ground to a halt.
Massa then usurped Hamilton momentarily with a 1:18.537 lap, but his superiority was fleeting, for the Briton replied with a 1:17.601 almost immediately.
Despite both Massa and Alonso improving their times, Hamilton maintained a six tenths of a second advantage until his teammate bolted on a set of super-softs on the one-hour mark and lapped in 1:16.973, 0.628 seconds clear of the field.
The leading positions remained static for the final half hour, but the Ferraris were pushed down to fifth and eighth as others made late improvements.
BMW's Nick Heidfeld, who had earlier abandoned a fast lap after a wild trip across the chicane kerbs, ended up third, ahead of Renault's Giancarlo Fisichella.
But moments after setting the fourth fastest time, Fisichella went straight on into the Sainte Devote barrier after clipping the inside kerb too heavily, ending his session.
Kimi Raikkonen finished practice in fifth place, with teammate Massa down in eighth, demoted by Mark Webber and Nico Rosberg in the closing moments. Webber then slowed with a left rear puncture after setting his fast lap.
Robert Kubica and Rubens Barrichello completed the top ten, while Scott Speed got as high as eighth for Toro Rosso before falling to 12th behind Alex Wurz.
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