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The contest began as a tight affair between the two competitors as both players remained stubborn on serve, which resulted in an eventual tie-break.
Dimitrov lost his first point in the decider, which set the tone, as Dolgopolov clinched the tie-break 7-3 to take a one-set lead at the All England Club.
Dimitrov managed to bounce back in the second set to earn a break, which was all that he needed to remain on top and draw level on sets.
The 23-year-old almost saved five break points, but Dolgopolov continued to battle through to earn a break and swing the momentum in his direction as he secured a further break to take a 2-1 set lead.
Games went by way of serve in the fourth set, but Dimitrov pushed his opponent to the limit and was eventually rewarded with a break, which allowed him to take the contest into a fifth and final set.
It was the perfect start for Dimitrov as he stormed to a 3-1 lead in the decider, leaving Dolgopolov to catch up, but the Bulgarian maintained his composure to earn two more breaks and eventually wrap up the match.