#4 Winning a calendar-year Grand Slam
In 2019, Federer played all four Grand Slam tournaments for the first time since 2015. The Swiss maestro's last Grand Slam title was at the Australian Open in 2018, where he won a record-extending 20th Grand Slam title.
At the French Open, Federer hasn't made the final since 2011, which was his fifth title match on the Parisian clay. The Swiss maestro won his lone Roland Garros title in 2009.
In each of the four other years he reached the final, he was thwarted by Rafael Nadal. Federer's 2019 Roland Garros semifinal (lost to Nadal) was his first at the tournament in seven years (since 2012, where he lost to Novak Djokovic).
Federer is usually at his imperious best at Wimbledon. The record eight-time champion was twice a swing of his racquet away from winning a ninth title this year, only to be thwarted by Djokovic in a historic first-ever Wimbledon fifth-set tiebreak.
Flushing Meadows has been a tournament of diminishing returns over the years for Federer. The Swiss won the last of his five (consecutive) titles at the last Major of the year in 2008. Since then, Federer has only reached two other title matches - 2009 (lost to Juan Martin del Potro) and 2015 (lost to Djokovic).
Wimbledon remains Federer's best bet to add to his Grand Slam tally, followed by the Australian Open. The US Open and the French Open, in that order, are probably the least likely places for Federer to win another Grand Slam title.
Going forward, the possibility of Federer reaching all four Grand Slam finals in the same year is a very remote possibility, let alone the Swiss maestro going all the way at each tournament in the same year.
The same also applies to the Swiss maestro's chances of becoming the first player in the Open Era to win each of the four Grand Slam tournaments multiple times. Nadal at the French Open is the biggest impediment in the path of Federer accomplishing this milestone.
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