Biggest timespan between 2 titles
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| # | Player | First Tournament | First Date | Last Tournament | Last Date | Timespan |
|---|---|---|---|---|---|---|
| 1 |  Jimmy Connors | Jacksonville | 1972-01-12 | Tel Aviv | 1989-10-16 | 6487d (17y 282d) |
| 2 |  Jaime Fillol Sr. | Indianapolis | 1968-07-08 | Itaparica | 1982-11-22 | 5250d (14y 140d) |
| 3 |  Manuel Orantes | Macon | 1969-02-17 | Bournemouth | 1982-04-19 | 4809d (13y 64d) |
| 4 |  Vijay Amritraj | Bretton Woods | 1973-07-23 | Bristol | 1986-06-16 | 4711d (12y 331d) |
| 5 |  John Alexander | London-3 | 1970-11-12 | Auckland | 1983-01-10 | 4442d (12y 62d) |
| 6 |  Tom Okker | Kingston | 1968-02-26 | Tel Aviv | 1979-10-08 | 4242d (11y 227d) |
| 7 | Marty Riessen | Bloemfontein | 1968-01-08 | Lafayette | 1979-07-30 | 4221d (11y 206d) |
| 8 | Stan Smith | Berkeley | 1968-09-22 | Frankfurt WCT | 1980-03-17 | 4194d (11y 179d) |
| 9 |  Boris Becker | Queen's Club | 1985-06-10 | Grand Slam Cup | 1996-12-03 | 4194d (11y 179d) |
| 10 | John McEnroe | Hartford | 1978-09-18 | Indianapolis | 1989-08-07 | 3976d (10y 326d) |
| 11 | Arthur Ashe | Richmond | 1968-02-02 | Los Angeles | 1978-09-18 | 3881d (10y 231d) |
| 12 | Brian Gottfried | Johannesburg WCT | 1973-04-14 | Vienna | 1983-10-17 | 3838d (10y 188d) |
| 13 | Sandy Mayer | Birmingham | 1973-01-15 | Gstaad | 1983-07-04 | 3822d (10y 172d) |
| 14 | Tony Roche | Sydney WCT | 1968-01-20 | Queen's Club | 1978-06-19 | 3803d (10y 153d) |
| 15 | Robert Lutz | Manchester | 1970-06-01 | Cologne | 1980-10-27 | 3801d (10y 151d) |
| 16 | Cliff Richey | Salisbury | 1968-02-12 | Johannesburg-1 | 1978-04-03 | 3703d (10y 53d) |
| 17 | Vitas Gerulaitis | Vienna | 1974-10-28 | Treviso | 1984-11-12 | 3668d (10y 18d) |
| 18 |  Cliff Drysdale | New Orleans WCT | 1968-02-16 | Baltimore | 1978-01-16 | 3622d (9y 337d) |
| 19 |  Ilie Nastase | Barranquilla | 1969-03-10 | WCT Challenge Cup | 1978-12-12 | 3564d (9y 279d) |
| 20 |  Guillermo Vilas | Buenos Aires | 1973-11-19 | Kitzbuhel | 1983-07-18 | 3528d (9y 243d) |