At the other end, Maccarone hit the same post twice - meaning Boro still ended the game without a shot on target.
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Jimmy Floyd Hasselbaink came off the bench to score Boro's third goal before fellow substitute Massimo Maccarone netted the winner at the death.
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Both sides made half-time changes, with Massimo Maccarone coming on for James Morrison and former Spurs striker Kanoute coming on for Javier Saviola.
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"We were preparing for a long, systematic search of thousands of globular clusters with the hope of finding just one black hole, " said Dr Maccarone.
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Siena battled on gamely, and on 26 minutes Massimo Maccarone escaped three defenders on the edge of the Milan box to bundle through before firing over on the stretch as Thiago Silva came across to put him under pressure.
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