But it was a different experience this time for Murray, who turns 22 on Friday, now that the event has moved to his least-favoured surface of clay.
Having lost on clay in the second round of the Rome Masters two weeks ago, the signs were not always good in a first set that lasted over an hour and went to a gruelling tie-break.
Murray grabbed a 4-2 lead before Bolelli fought back and earned two set points, but the third seed stayed calm and came through thanks to a long forehand from the 23-year-old Italian.
The second set followed a similar pattern, although Bolelli did have a break point on the seventh game that he failed to convert.
And went it came to the crunch 10th game experience was the difference, with Bolelli surviving one break point by firing down an ace but failing to save the next when he struck his effort into the net.
"I felt fairly good on the court, I hardly missed a ball the whole match," said Murray. "The first set was tough. I played some good points and overall was very happy with how I played."
Murray won in Madrid last year when the event was indoors on hard courts
The British number one said he had taken a leaf out of Rafael Nadal's book, having practised with the world number one earlier in the week.
"If you watch someone like Rafa at the start of matches you will see him a long way behind the baseline making a lot of balls, trying to play solid and the more confidence he gets he moves closer and closer to the baseline, and that's what I did today."
And Murray expects another tough test from the experienced Robredo.
"Tommy moves well and puts in high percentage of first serves," said Murray.
"He has a great forehand like many of the Spanish players. He rarely gives away much in a match. But I like the conditions here, they're much quicker than other clay surfaces I've played on in the last few weeks. I have to use my serve well though."
Meanwhile, Federer began his campaign with a straightforward win 6-1 7-5 over Sweden's Robin Soderling.
"It's about playing well and getting ready for Paris," said the Swiss. "It's good to get through the first match and hopefully build on this and play a bit better in my next match."
Verdasco eased into the third round, breaking the serve of fellow Spaniard Juan Carlos Ferrero five times en route to a 6-3 6-2 victory.
Croatia's Ljubicic upset Frenchman Tsonga 6-4 7-5, while Spaniard Robredo beat American Mardy Fish 3-6 7-6 (7-5) 6-2 and Russian 10th seed Nikolay Davydenko beat Viktor Troicki of Serbia 6-2 6-2.
Top seed Nadal faces Juergen Melzer on Wednesday after the Austrian defeated Albert Montanes 4-6 7-5 6-3.
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