| Year | date | Winner | sets | Finalist | set 1 | set 2 | set 3 |
| 2018 Men Delray Beach USA | 25.02 | Frances Tiafoe |  USA | WC | 2-0 | Peter Gojowczyk |  GER | | 6-1 | 6-4 | |
| 2017 Men Delray Beach USA | 26.02 | Jack Sock | USA | 3 | wo | Milos Raonic |  CAN | 1 | walk over |
| 2016 Men Delray Beach USA | 21.02 | Sam Querrey | USA | | 2-0 | Rajeev Ram | USA | | 6-4 | 6-66 | |
| 2015 Men Delray Beach USA | --.-- | Ivo Karlovic |  CRO | 4 | 2-0 | Donald Young | USA | | 6-3 | 6-3 | |
| 2014 Men Delray Beach USA | --.-- | Marin Cilic | CRO | 7 | 2-1 | Kevin Anderson |  RSA | 4 | 7-66 | 6-77 | 6-4 |
| 2013 Men Delray Beach USA | --.-- | Ernests Gulbis |  LAT | Q | 2-0 | Edouard Roger-Vasselin |  FRA | | 7-63 | 6-3 | |
| 2012 Men Delray Beach USA | --.-- | Kevin Anderson | RSA | 7 | 2-0 | Marinko Matosevic |  AUS | Q | 6-4 | 7-62 | |
| 2011 Men Delray Beach USA | --.-- | Juan Martin Del Potro |  ARG | SE | 2-0 | Janko Tipsarevic |  SRB | 6 | 6-4 | 6-4 | |
| 2010 Men Delray Beach USA | --.-- | Ernests Gulbis | LAT | | 2-0 | Ivo Karlovic | CRO | 2 | 6-2 | 6-3 | |
| 2009 Men Delray Beach USA | --.-- | Mardy Fish | USA | 1 | 2-0 | Evgeny Korolev |  KAZ | Q | 7-5 | 6-3 | |
| 2008 Men Delray Beach USA | --.-- | Kei Nishikori |  JPN | Q | 2-1 | James Blake | USA | 1 | 3-6 | 6-1 | 6-4 |
| 2007 Men Delray Beach USA | --.-- | Xavier Malisse |  BEL | 3 | 2-1 | James Blake | USA | 1 | 5-7 | 6-4 | 6-4 |
| 2006 Men Delray Beach USA | --.-- | Tommy Haas | GER | 4 | 2-1 | Xavier Malisse | BEL | 3 | 6-3 | 3-6 | 7-65 |
| 2005 Men Delray Beach USA | --.-- | Xavier Malisse | BEL | 3 | 2-0 | Jiri Novak |  CZE | 2 | 7-66 | 6-2 | |
| 2004 Men Delray Beach USA | --.-- | Ricardo Mello |  BRA | | 2-0 | Vince Spadea | USA | 1 | 7-62 | 6-3 | |
| 2003 Men Delray Beach USA | --.-- | Jan-Michael Gambill | USA | 4 | 2-0 | Mardy Fish | USA | | 6-0 | 7-65 | |
| 2002 Men Delray Beach USA | --.-- | Davide Sanguinetti |  ITA | 5 | 2-1 | Andy Roddick | USA | 1 | 6-4 | 4-6 | 6-4 |
| 2001 Men Delray Beach USA | --.-- | Jan-Michael Gambill | USA | 4 | 2-0 | Xavier Malisse | BEL | SE | 7-5 | 6-4 | |
| 2000 Men Delray Beach USA | --.-- | Stefan Koubek |  AUT | 6 | 2-1 | Alex Calatrava |  ESP | Q | 6-1 | 4-6 | 6-4 |
| 1999 Men Delray Beach USA | --.-- | Lleyton Hewitt | AUS | 6 | 2-1 | Xavier Malisse | BEL | WC | 6-4 | 6-7 | 6-1 |
