Day one of the Chess.com Open Playoffs reduced the winners' side to four players, as Magnus Carlsen, Denis Lazavik, Jan-Krzysztof Duda and Nihal Sarin each advanced after two match victories.
The event follows a 16-player double-elimination format, allowing competitors to remain in contention until a second match defeat. Matches are played at a 10-minute time control without increment, with four-game contests in the Winners Bracket and two-game matches in the Losers Bracket. The top three finishers will earn places at the Esports World Cup, although already-qualified players - Carlsen, Alireza Firouzja and Lazavik - do not pass on additional qualifying spots if they finish in those positions.
Carlsen's progress was the most straightforward among the four. He required only three games in each of his matches, first overcoming Shant Sargsyan by winning the opening two games before drawing the third. His second encounter followed a similar pattern, as he dispatched Vincent Keymer efficiently. Keymer had reached that stage by eliminating Pranesh M in equally convincing fashion, but was unable to slow Carlsen's momentum.
Duda also produced a strong showing, albeit via a more eventful route. He began his campaign with a loss against Ian Nepomniachtchi but recovered immediately, winning the next three games to secure the match. In the following round, he drew the opener against Sina Movahed before claiming the next two games. The deciding game featured a notable piece sacrifice.
Lazavik’s path was considerably tighter. His opening match against Yu Yangyi remained level through three draws before being decided in the fourth game, where Lazavik exploited a tactical opportunity to trap his opponent's queen. He then faced Nodirbek Abdusattorov in a closely fought contest that ultimately required an Armageddon decider, in which Lazavik prevailed with the white pieces.
Nihal Sarin also remained on the winners' side after two demanding matches. He secured a relatively smooth victory over Maxime Vachier-Lagrave by winning the first two games and drawing the third. His subsequent match against Daniil Dubov proved more balanced, with all classical games drawn before Nihal edged the Armageddon game to advance.

In the Losers Bracket, four players were eliminated on the opening day: Shant Sargsyan, Sam Sevian, Arjun Erigaisi and World Championshp challenger Javokhir Sindarov. Dubov's 3–0 victory over Sindarov in the initial round stood out, while Pranesh M was the only player to win his elimination match without requiring a tiebreak, defeating Sargsyan 2–0 through precise endgame play. The remaining matches extended to Armageddon, including Yu's narrow win over Sevian.
One of the more notable pairings saw Sindarov face Vachier-Lagrave, with both players recently associated with Team Vitality. Despite losing the first game, Vachier-Lagrave recovered to win the next two and remain in contention. Nepomniachtchi followed a similar pattern, overturning an early loss to defeat Arjun Erigaisi.
By the end of the day, eight players remained in the Losers Bracket, while the Winners Bracket was reduced to four contenders still unbeaten in match play.

| Date | Event |
| Apr 23 | Round of 16 |
| Apr 23 | Winners QF/ Losers R1 |
| Apr 24 | Winners SF/Losers R2 |
| Apr 24 | Winners Final/Losers R3 |
| Apr 25 | Losers QF |
| Apr 25 | Losers SF |
| Apr 25 | Losers Final |
| Apr 26 | Grand Final |
| Apr 26 | Grand Final Reset |