The day did not start well, with the Bermuda Weather Service issuing a Severe Weather Watch with a Thunderstorm Advisory and Gale Warning, which delayed matches up to three hours.
Once the day did get underway, players were challenged with a strong wind and sand blowing, plus their opponent.
Simons took on Trey Mallory in the first A Division Semi-Final. The pair who battled in the Manders Tennis Management Masters Invitational Final back in December would once again have spectators on an edge.
Much like they did back in December the pair would hold their serves early, but Simons would eventually win the first set 6-3.
The second set would see the pair level at 3-3, with Mallory serving, Simons would break to make it 4-3, both would then hold their next serves with Simons leading 5-4, but Mallory would break to get it to 5-5, Simons would then take a 6-5 lead after breaking Mallory, but once again Mallory would break Simons to make it 6-6 and send it to a tie-breaker. Mallory would jump out to a 4 – 0 lead, but Simons would fight back to make it 4-4, both players would have a chance to serve out the match. Simons would eventually win the second set 10-8 in the tie-breaker, with a serve and volley.
The second Semi-Final would see Phillips taking on Gavin Manders.
Phillips would hold a 2–1 lead after the first three games in the first set, the score then moved to 4-3 after seven games, Phillips would eventually win the first set 6-3.
Phillips would jump out to a 4-0 lead, he would then break Manders for the third time in the set to claim a 6-0 second set win.