| Chubb Classic | ||
|---|---|---|
| TORNEO SENIOR MASCHILE |
Aetna Challenge
| 1988 | Gary PLAYER (RSA) | The Club at Pelican Bay |
|---|---|---|
| 1989 | Gene LITTLER (USA) | The Club at Pelican Bay |
| 1990 | Lee TREVINO (USA) | The Club at Pelican Bay |
| 1991 | Lee TREVINO (USA) | The Vineyards Golf and Country Club |
| 1992 | Jimmy POWELL (USA) | The Vineyards Golf and Country Club |
Better Homes & Gardens Real Estate Challenge
| 1993 | Mike HILL (USA) | The Vineyards Golf and Country Club |
|---|
IntelliNet Challenge
| 1994 | Mike HILL (USA) | The Vineyards Golf and Country Club |
|---|---|---|
| 1995 | Bob MURPHY (USA) | The Vineyards Golf and Country Club |
Greater Naples IntelliNet Challenge
| 1996 | Al GEIBERGER (USA) | The Classics at Lely Resort |
|---|
LG Championship
| 1997 | Hale IRWIN (USA) | Bay Colony Golf Club |
|---|---|---|
| 1998 | Gil MORGAN (USA) | Bay Colony Golf Club |
ACE Group Classic
| 1999 | Allen DOYLE (USA) | Bay Colony Golf Club |
|---|---|---|
| 2000 | Lanny WADKINS (USA) | Pelican Marsh Golf Club |
| 2001 | Gil MORGAN (USA) | Pelican Marsh Golf Club |
| 2002 | Hale IRWIN (USA) | The TwinEagles Club (Talon Course) |
| 2003 | Vicente FERNANDEZ (ARG) | The TwinEagles Club (Talon Course) |
| 2004 | Craig STADLER (USA) | The TwinEagles Club (Talon Course) |
| 2005 | Mark JAMES (ENG) | The TwinEagles Club (Talon Course) |
| 2006 | Loren ROBERTS (USA) | The TwinEagles Club (Talon Course) |
| 2007 | Bobby WADKINS (USA) | Quail West Golf and Country Club |
| 2008 | Scott HOCH (USA) | Quail West Golf and Country Club |
| 2009 | Loren ROBERTS (USA) | TPC Treviso Bay |
| 2010 | Fred COUPLES (USA) | The Quarry |
| 2011 | Bernhard LANGER (GER) | The Quarry |
| 2012 | Kenny PERRY (USA) | The TwinEagles Club (Talon Course) |
| 2013 | Bernhard LANGER (GER) | The TwinEagles Club (Talon Course) |
| 2014 | Kirk TRIPLETT (USA) | The TwinEagles Club (Talon Course) |
| 2015 | Lee JANZEN (USA) | The TwinEagles Club (Talon Course) |
Chubb Classic
| 2016 | Bernhard LANGER (GER) | The TwinEagles Club (Talon Course) |
|---|---|---|
| 2017 | Fred COUPLES (USA) | The TwinEagles Club (Talon Course) |
| 2018 | Joe DURANT (USA) | The TwinEagles Club (Talon Course) |
| 2019 | Miguel Angel JIMENEZ (SPA) | The Classics at Lely Resort |
| 2020 | Scott PAREL (USA) | The Classics at Lely Resort |
| 2021 | Steve STRICKER (USA) | Tiburon Golf Club (Black Course) |
| 2022 | Bernhard LANGER (GER) | Tiburon Golf Club (Black Course) |
| 2023 | Bernhard LANGER (GER) | Tiburon Golf Club (Black Course) |
| 2024 | Stephen AMES (CAN) | Tiburon Golf Club (Black Course) |
| 2025 | Justin LEONARD (USA) | Tiburon Golf Club (Black Course) |
| 2026 | David TOMS (USA) | Tiburon Golf Club (Black Course) |