Why are my if statements not working in this tic tac toe game?

I am working on a tic tac toe program in C#. Part of my code is supposed to use if statements that will announce the winner when a player has won. However, when I run the code, it doesn't work. When the player wins, regardless of the combination, the MessageBox never pops up. Does anyone know why? This is my code:

using System;
using System.Collections.Generic;
using System.ComponentModel;
using System.Data;
using System.Drawing;
using System.Linq;
using System.Text;
using System.Threading.Tasks;
using System.Windows.Forms;

namespace TicTacToeV1
{
    public partial class Form1 : Form
    {
        private const string player1 = "Player 1's Turn";
        private const string player2 = "Player 2's Turn";

        public Form1()
        {
            InitializeComponent();
        }

        private void gameBoxPictureBox_Click(object sender, EventArgs e)
        {
            PictureBox gamePictureBox = (PictureBox)sender;

            if(playerTrunLabel.Text == player1)
            {
                gamePictureBox.Image = Properties.Resources.X_150;
                playerTrunLabel.Text = player2;
                timeLabel.Text = "10";

            }
            else
            {
                gamePictureBox.Image = Properties.Resources.O_150;
                playerTrunLabel.Text = player1;
                timeLabel.Text = "10";
            }
            if (gameBox1PictureBox.Image == Properties.Resources.X_150)
            {
                if (gameBox2PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox3PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
                if (gameBox4PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox7PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
                if (gameBox5PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
            }
            if (gameBox2PictureBox.Image == Properties.Resources.X_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox8PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
            }
            if (gameBox3PictureBox.Image == Properties.Resources.X_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox7PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
                if (gameBox6PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
            }
            if (gameBox4PictureBox.Image == Properties.Resources.X_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox6PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
            }
            if (gameBox7PictureBox.Image == Properties.Resources.X_150)
            {
                if (gameBox8PictureBox.Image == Properties.Resources.X_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.X_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 1 wins the game!");
                    }
                }
            }
            if (gameBox1PictureBox.Image == Properties.Resources.O_150)
            {
                if (gameBox2PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox3PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
                if (gameBox4PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox7PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
                if (gameBox5PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
            }
            if (gameBox2PictureBox.Image == Properties.Resources.O_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox8PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
            }
            if (gameBox3PictureBox.Image == Properties.Resources.O_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox7PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
                if (gameBox6PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
            }
            if (gameBox4PictureBox.Image == Properties.Resources.O_150)
            {
                if (gameBox5PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox6PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
            }
            if (gameBox7PictureBox.Image == Properties.Resources.O_150)
            {
                if (gameBox8PictureBox.Image == Properties.Resources.O_150)
                {
                    if (gameBox9PictureBox.Image == Properties.Resources.O_150)
                    {
                        playerTime.Stop();
                        startButton.Visible = false;
                        MessageBox.Show("Player 2 wins the game!");
                    }
                }
            }
        }

        private void clearButton_Click(object sender, EventArgs e)
        {
            gameBox1PictureBox.Image = null;
            gameBox2PictureBox.Image = null;
            gameBox3PictureBox.Image = null;
            gameBox4PictureBox.Image = null;
            gameBox5PictureBox.Image = null;
            gameBox6PictureBox.Image = null;
            gameBox7PictureBox.Image = null;
            gameBox8PictureBox.Image = null;
            gameBox9PictureBox.Image = null;
            startButton.Visible = true;
            playerTrunLabel.Text = player1;
            playerTime.Start();
            timeLabel.Text = "10";
        }

        private void exitButton_Click(object sender, EventArgs e)
        {
            this.Close();
        }

        private void startButton_Click(object sender, EventArgs e)
        {
            playerTime.Start();
        }

        private void playerTime_Tick(object sender, EventArgs e)
        {
            int time = int.Parse(timeLabel.Text);
            timeLabel.Text = (--time).ToString();
            if (timeLabel.Text == "0")
            {
                timeLabel.Text = "10";
                if (playerTrunLabel.Text == player1)
                {
                    playerTrunLabel.Text = player2;
                }
                else
                {
                    playerTrunLabel.Text = player1;
                }
            }
        }
    }
}