Holy Week: Five Day Devotional
- Pastor Dexter B. Upshaw Jr.

- Mar 29
- 9 min read

Here are a few additional resources to guide your quiet time this week:
Watch the replay of "What Kind of King is This?" by Pastor Dexter B. Upshaw Jr.
Use this small group discussion guide with family, friends, and co-workers.
Join us for our 6 AM Prayer Call, Monday through Friday (EST)
Day 1: Holy Monday
Holy Week Devotional
"Then Jesus went into the temple of God and drove out all those who bought and sold in the temple, and overturned the tables of the money changers and the seats of those who sold doves. And He said to them, 'It is written, "My house shall be called a house of prayer," but you have made it a den of thieves." - Matthew 21:12–13
Devotional: Holy Week doesn't begin with quiet reflection; it begins with action. On Holy Monday, we commemorate how Jesus entered the Temple courts and overturned tables. This wasn't a moment of lost composure. It was holy zeal. He was the Messiah, and He was taking authority in His Father's house.
The Temple had drifted from its purpose. Jews coming to worship from all parts of the world needed animals for sacrifice and proper currency for the Temple tax. Some scholars believe money was exchanged and animals were sold at exorbitant prices, for the profit of the priesthood. Against this backdrop, Jesus looked at that and refused to let it stand. Isaiah said God's house would be a house of prayer for all nations (Isaiah 56:7). That vision had been reduced to a predatory marketplace, a den of thieves.
This episode isn't just a historical account—it has personal implications. Here's where this lands for us: Scripture says we are now the temple of the Holy Spirit (1 Corinthians 6:19). Just as Jesus insisted the Temple be restored to God's purpose, we are called to examine our own hearts. What unauthorized activities have we allowed to move in and take up space that belongs to God? Pride, busyness, bitterness, unforgiveness, greed, lust, jealousy, and distraction; these things don't announce themselves. They settle in quietly and take up residence in the sacred spaces of our hearts.
When God starts flipping tables in your heart, repent with humility and allow Him to restore you to your original purpose. The challenge of Holy Monday is to let God reclaim His space in us, making us again what we are meant to be.
Question: What has slowly taken over the sacred space of your inner life? What would it mean, practically, to invite the Lord to change it today?
Prayer: Lord Jesus, Your zeal for Your house hasn't changed. Walk through the temple of my heart today and take authority over what doesn't belong there. I'm not asking You to bless the clutter — I'm asking You to clear it. Make me a place of genuine prayer and real communion. Set me apart for Your presence alone. In Your name, Amen.
Day 2: Holy Tuesday
Holy Week Devotional
"Jesus said to him, '"You shall love the Lord your God with all your heart, with all your soul, and with all your mind." This is the first and great commandment. And the second is like it: "You shall love your neighbor as yourself." On these two commandments hang all the Law and the Prophets.'"- Matthew 22:37–40
Devotional: Holy Tuesday commemorates the moment when the Pharisees, Sadducees, Herodians, and scribes came to Jesus one after another with questions designed to trap Him. Not one of them succeeded. After silencing every faction, Jesus asked a question of His own — and nobody could answer it. What they intended as an ambush, He turned into a classroom.
When a lawyer asked about the greatest commandment, Jesus didn't navigate the complexities of the 613 Mosaic laws. Instead, He went straight to the foundation: love God fully and love your neighbor sincerely. Then He made a statement that should stop us cold—every law and every prophetic word in Scripture hangs on those two commands.
That's not a reduction; that's a revelation. In other words, every commandment about worship expresses love for God, while every commandment about justice and honesty expresses love for our neighbor. Once you understand the two great commandments, you hold the interpretive key to the whole Bible. Theology that doesn't end in love has missed the point.
Paul says in Romans 13:10 that love fulfills the law. He doesn't mean love replaces obedience. He means authentic obedience comes from love. One who truly loves God will honor His commands. One who truly loves their neighbor won't deceive or harm them. Love isn't a lower standard, but the source of the standard.
Is love for God actually driving your life, or has it quietly become background noise? You can be busy, faithful in attendance, and doctrinally sound, yet still miss the first commandment. God isn't looking for performance. He's looking for a heart that is genuinely, increasingly His.
Question: Be honest about the orientation of your daily life. Is your love for God at the center of your routine, or has it become an assumption you carry rather than a reality you actively pursue?
Prayer: Father, forgive me for any way I have failed to love You with my whole heart. Ignite something genuine within me—something more than mere compliance; a true affection for who You are. From that place, teach me to see the people around me as You do. Let love be the reason I obey and serve. Through Christ my Lord, Amen.
Day 3: Spy Wednesday
Holy Week Devotional
"Then one of the twelve, called Judas Iscariot, went to the chief priests and said, 'What are you willing to give me if I deliver Him to you?' And they counted out to him thirty pieces of silver. So from that time he sought opportunity to betray Him." - Matthew 26:14–16
Devotional: On Spy Wednesday, we remember the betrayer. Judas Iscariot, one of the twelve, slipped away and said to the chief priests, "What will you pay me to hand Jesus over?" They agreed on thirty silver pieces—the price of a slave under Mosaic law (Exodus 21:32). From then on, Judas watched for his chance.
What makes this so jarring is proximity. Judas wasn't an outsider; he had walked with Jesus for three years. He heard the Sermon on the Mount, witnessed the feeding of the five thousand, and saw the dead raised. He even carried the group's money (John 12:6). Yet something in him had already made up his mind. The betrayal didn't begin with the priests. It began earlier—in a heart never fully surrendered.
Zechariah prophesied that the Messiah would be sold for thirty pieces of silver and thrown back into the house of the Lord (Zechariah 11:12–13). Judas’s action did not catch God by surprise. His betrayal was known and woven into the redemptive plan. That doesn't excuse Judas. Jesus said plainly it would have been better for that man not to have been born (Matthew 26:24). But it reminds us that no act of human treachery can derail what God has purposed.
Spy Wednesday presses a hard, honest truth: being near Jesus is not the same as being changed by Him. Judas had access to, knowledge of, and a history with Christ. Still, he lived at a distance in his soul. Each generation of the Church must heed this warning. We can press close to the holy and remain unchanged. Religion without relationship is a shell. Nearness without surrender, a haunting emptiness.
This Wednesday invites honest self-examination. Not suspicion or condemnation — but the kind of searching question the disciples asked when Jesus announced a betrayer at the table: "Lord, is it I?" (Matthew 26:22). Satan may have entered the heart of Judas, but refuse to allow him to fill you.
Question: The disciples asked with aching uncertainty, "Lord, is it I?" Is there any place within your heart where you have the potential to betray or sell out Jesus?
Prayer: Lord Jesus, search the silent corners of my heart today and forgive me for any way I have been disloyal to You. You knew Judas would betray You, yet You washed his feet anyway. Thank you for the love you show me, even when I fall short of Your glory. Guard my heart from the deceit of the enemy. In Your name, Amen.
Day 4: Maundy Thursday
Holy Week Devotional
"And He took bread, gave thanks and broke it, and gave it to them, saying, 'This is My body which is given for you; do this in remembrance of Me.' Likewise He also took the cup after supper, saying, 'This cup is the new covenant in My blood, which is shed for you.'"- Luke 22:19–20
Devotional: Today is Maundy Thursday. Maundy simply means “to mandate.” On this day, we commemorate the last supper and Jesus’s mandate to the disciples to love one another.
On the night of His betrayal, Jesus gathered with His disciples for the Passover—a meal commemorating Israel's deliverance. Each element on the table carried deep history, setting the stage for Jesus to give the meal new meaning. When Jesus picked up the bread, He explained that what the Passover had pointed to for generations, He was about to fulfill.
Notice the language: "His body is given; His blood is shed." Not taken — given. This shift matters: Jesus was no helpless victim. He willingly offered Himself, laying down His life on purpose (John 10:18). The Last Supper foreshadowed the cross, interpreted by the one who would hang on it. He wasn't just predicting what would happen — He was telling us what it meant.
When He said "new covenant," Jesus invoked Jeremiah 31:31–34, where God promised a covenant written on human hearts, secured by His initiative rather than our faithfulness. At that table, Jesus announced that the hour of that promise had arrived. Its seal would be His own blood—not the blood of animals, but the blood of the Son of God.
After supper, another key transition occurred. Jesus washed the disciples' feet, delivered His farewell discourse across four chapters in John, and prayed for unity, protection, and the generations who would believe through the disciples' testimony. In His final hours before arrest, His attention was entirely on others.
Similarly, each time the church gathers around the bread and cup, it's more than a ritual—it's a declaration. Paul says in 1 Corinthians 11:26: " We proclaim the Lord's death until He comes. Communion is theology lived, announcing that God gave His Son, the Son gave Himself, and that giving was enough.
Question: When you receive Communion, how do you experience it—personally, spiritually, or habitually? In what ways could you intentionally approach the table to encounter Christ more deeply?
Prayer: Lord Jesus, on the night You were betrayed, You gave thanks. I can barely take that in. Teach me to receive what You've given with the weight it deserves. When I come to Your table, don't let it be routine. Let the bread and cup remind me of what love looks like when it costs everything — given, not taken; poured out, not withheld. I receive Your covenant mercy right now. Amen.
Day 5: Good Friday
Holy Week Devotional
"So when Jesus had received the sour wine, He said, 'It is finished!' And bowing His head, He gave up His spirit." -John 19:30
Devotional: Good Friday doesn't ask us to admire a martyr. It asks us to face an atoning sacrifice. Jesus didn't die because Rome overpowered Him—He chose to bear our judgment. The cross is where God's righteousness and mercy met in one act. The weight of what happened there can't be reduced to sentiment.
"It is finished" is one word in Greek: tetelestai. A craftsman wrote it on completed work; a merchant stamped it on paid debt. Jesus didn't whisper it—He declared it, marking His mission done. The mission wasn't cut short by the cross; it was completed there. Every sacrifice since Eden, every act of the High Priest in the Temple, and every prophecy of the suffering Servant built toward this moment.
When He died, the Temple veil tore from top to bottom (Matthew 27:51). This thick curtain separated the Holy of Holies from everyone except the High Priest on the Day of Atonement. Top to bottom— not torn by human hands from below, but from above. God Himself removed the barrier. Access to His presence was no longer restricted by a system. Jesus’s death afforded full access to the Father.
To grasp these events, remember the underlying theology: substitutionary atonement. Isaiah 53 says the Servant would bear our iniquity—that the punishment securing our peace would fall on Him. Peter writes: Christ died for sins once for all, the righteous for the unrighteous, to bring us to God (1 Peter 3:18). The cross doesn't minimize sin. It shows how seriously God treats it—and how far His love goes.
This day is called Good Friday because of what was accomplished, not what was suffered. Because He died, we can be acquitted. Because the debt has been paid, the debtor is free. Because He gave up His spirit, the Spirit can be given. There is no Resurrection Sunday without Good Friday. The church doesn't skip this day on the way to Sunday — we walk through it, and on the other side, we find our life.
Question: Do you rush past the cross toward the resurrection? What does "finished" mean for the guilt, shame, or debt you carry?
Prayer: Father, I acknowledge my sins. The debt Jesus paid was mine. The judgment He carried was what my sin deserved. Because of His sacrifice, it is finished, completely and forever. Nothing can be added to what He did. Don't let me grow numb to what it cost You to rescue me. In the name of Jesus, crucified and risen, Amen.




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