Historical clue formulations

• Play ___ (sit in with the band) — 2023-06-23
• For ___ amount of time — 2020-08-02
• Play ___ (perform with the band) — 2016-05-05
• "I hate to break up ___" — 2013-02-12
• At ___ time (prearranged) — 2011-11-25
• Play ___ (enjoy some tennis) — 2011-09-07
• Play ___ (do some tennis) — 2011-05-27
• "I'd hate to break up ___" — 2010-12-21
• "Win ___ of ..." (contest come-on) — 2009-05-24
• Play ___ (do some tennis) — 2009-01-15
• Play ___ (enjoy some tennis) — 2008-06-10
• Warhol's "___ of Six Self-Portraits" — 2008-05-25
• "___ of Six" (Joseph Conrad story collection) — 2008-05-11
• "I'd hate to break up ___" — 2008-03-02
• "___ of Six" (Joseph Conrad story collection) — 2007-12-28
• "I'd hate to break up ___" — 2005-11-28
• "I'd hate to break up ___" — 2005-01-09
• Playing ___ (court activity) — 2004-12-22
• Play ___ (do some tennis) — 2002-06-17
• "I'd hate to break up ___" — 1998-06-14
• "I'd hate to break up ___" — 1996-08-05