Bolelli defeated Simon Greul 7-6 (7-4), 7-6 (7-4) in a match that took nearly 2 hours. Greul faced only one break point -- and lost it -- in the match but converted only 1-of-4 break opportunities against Bolelli. That gave Bolelli a chance to grab the match in the tie-breakers.
Pere Riba, another qualifier, advanced out of the first round with a 1-6, 6-0, 6-3 victory over Paul-Henri Mathieu. Riba won 63 percent of the points after the first set.
Florent Serra topped Evgeny Korolev 7-6, (9-7), 6-3 despite having to deal with 11 break-point situations. Also, Andrey Golubev stopped Mischa Zverev 7-5, 6-1 and Florian Mayer dropped Pablo Cuevas 6-4, 6-1.
Denis Istomin, Jan Hajek and Maximo Gonzalez each needed three sets to win Monday. Istomin got by Lukas Rosol 3-6, 6-4, 6-3; Hajek topped Andreas Beck 6-3, 4-6 7-5; and Gonzalez beat Olivier Rochus 6-4, 5-7, 6-2.
Other winners Monday were Jarkko Nieminen, Fabio Fognini, Potito Starace and Jeremy Chardy.
Swim Week Miami Beach 2014 [PHOTOS]