Let me know if it's the first situation, though, and I'll edit my post.
He eyes the other orc warily as it looks for a similar opening on the half-elf.
Rolls
War Pick Attack - (1d20+4)
(17) + 4 = 21
War Pick Damage - (1d8+2)
(7) + 2 = 9
War Pick Attack - (1d20+4)
(17) + 4 = 21
War Pick Damage - (1d8+2)
(7) + 2 = 9
Bowstaff attack vs Orc Leader (w/ adv) - (1d20+5, 1d20+5, 1d8+3)
1d20+5 : (11) + 5 = 16
1d20+5 : (4) + 5 = 9
1d8+3 : (4) + 3 = 7
Flurry of Blows 1 vs Orc Leader - (1d20+5, 1d4+3)
1d20+5 : (6) + 5 = 11
1d4+3 : (4) + 3 = 7
Flurry of Blows 2 vs Orc Leader - (1d20+5, 1d4+3)
1d20+5 : (8) + 5 = 13
1d4+3 : (2) + 3 = 5
Attack - (1D20+7)
(15) + 7 = 22
Damage - (2d6+5)
(62) + 5 = 13
Two-handed Hammer Fist (advantage from Reckless Attack) - (1d20+6, 1d20+6, 2d6+6)
1d20+6 : (20) + 6 = 26
1d20+6 : (17) + 6 = 23
2d6+6 : (54) + 6 = 15
Crit damage (Brutal Critical) - (2d6)
(52) = 7
Moar damage! - (1d6)
(6) = 6
Melee Spell Attack - (1d20+5)
(18) + 5 = 23
Damage: Necrotic - (3d10)
(1029) = 21
Spiritual Weapon Attack - (1d20+5)
(13) + 5 = 18
Spiritual Weapon Damage - (1d8+3)
(4) + 3 = 7
Orc 1 attack against Herod - (1D20+5)
(1) + 5 = 6
Orc 2 attack against Herod - (1D20+5)
(16) + 5 = 21
Herod's Damage (slashing) - (1D12+3)
(12) + 3 = 15
Orc 1 attack against Krigare - (1D20+5)
(17) + 5 = 22
Orc 2 attack against Krigare - (1D20+5)
(19) + 5 = 24
Krigare's damge 1 - (1D12+3)
(1) + 3 = 4
Krigare's damage 2 - (1D12+3)
(4) + 3 = 7
Orc leader fall damage - (1D6)
(2) = 2
Orc Leader's attack against Herod - (1D20+5)
(13) + 5 = 18
Orc leader's damage (piercing) - (1D6+3)
(5) + 3 = 8
Orc leader's damage (lightning) - (1D8)
(6) = 6
Orc attack against Herod - (1D20+5)
(3) + 5 = 8
Quarterstaff attack vs. Orc Leader (w/ adv) - (1d20+5, 1d20+5, 1d8+3)
1d20+5 : (3) + 5 = 8
1d20+5 : (8) + 5 = 13
1d8+3 : (8) + 3 = 11
Unarmed strike (knee) vs. Orc Leader - (1d20+5, 1d4+3)
1d20+5 : (10) + 5 = 15
1d4+3 : (2) + 3 = 5
Unarmed strike (kick) vs. Orc Leader - (1d20+5, 1d4+3)
1d20+5 : (6) + 5 = 11
1d4+3 : (4) + 3 = 7
Attack - (1d20+7)
(11) + 7 = 18
Damage - (2d6+5)
(46) + 5 = 15
Cure Wounds - (1d8+3)
(7) + 3 = 10
Spiritual Weapon - (1d20+5)
(3) + 5 = 8
Damage - (1d8+3)
(3) + 3 = 6
Homebrew Tides of Chaos - (1d20)
(2) = 2
War Pick Attack - (1d20+4)
(14) + 4 = 18
War Pick Damage - (1d8+2)
(7) + 2 = 9
Double-uppercut (advantage from Reckless Attack) - (1d20+6, 1d20+6, 2d6+6)
1d20+6 : (3) + 6 = 9
1d20+6 : (12) + 6 = 18
2d6+6 : (31) + 6 = 10
Orc attack against Tomas - (1D20+5)
(12) + 5 = 17
Orc attack against Krigare - (1D20+5)
(19) + 5 = 24
Krigare's damge (slashing) - (1D12+3)
(5) + 3 = 8
Orc leader's attack against Ronda - (1D20+5)
(6) + 5 = 11
Advantage - (1D20+5)
(11) + 5 = 16
Orc's attack against Ronda - (1D20+5)
(19) + 5 = 24
Advantage - (1D20+5)
(10) + 5 = 15
Floating Orc spear against Krigare - (1D20+5)
(3) + 5 = 8
Orc leader's damage (piercing) - (1D6+3)
(2) + 3 = 5
Orc's damage (Ronda) - (1D12+3)
(2) + 3 = 5
Orc leader's damage (lightning) - (1D8)
(4) = 4