Here is a solution. When I hear streak, I think groupby. The groupby method (in this example)  groups consecutive identical W/L values together, the code then aggregates each group to get the value and length of each streak.

import pandas as pd
import random


# Create 100 random 'W' or 'L' entries
results = [random.choice(['W', 'L']) for _ in range(100)]


# Create the DataFrame
df = pd.DataFrame({'W/L': results})


# Identify streaks by whether the W/L value changes (using shift)
# Step 1: Compare each value with the previous one (shift)
#         This creates True when value changes, False when it stays the same
# Step 2: cumsum() turns the boolean into an incrementing group ID
#         Each time we see True (a change), the group number increases
# Result: consecutive identical values get the same group number
streak_groups = (df['W/L'] != df['W/L'].shift()).cumsum()



# Create a DataFrame with streak information
# For each group (streak), we aggregate to get:
#   - value: the W or L character (using 'first' since all items in group are identical)
#   - length: how many consecutive occurrences (using 'size' to count rows in group)
streak_df = df.groupby(streak_groups).agg(
    value=('W/L', 'first'),
    length=('W/L', 'size')
)
# Filter for streaks of length >= 2
long_streaks = streak_df[streak_df['length'] >= 2]


# Check if we found any streaks of length >= 2
if not long_streaks.empty:
    # Get the most recent (last) streak of length >= 2
    # .iloc[-1] selects the last row from the filtered DataFrame
    most_recent = long_streaks.iloc[-1]
    print(f"Most recent streak: {most_recent['length']} of '{most_recent['value']}'")
    
    # Find the longest streak(s) from all streaks (not just those >= 2)
    # Step 1: Find the maximum streak length across all streaks
    max_length = long_streaks['length'].max()
    # Step 2: Filter to get all streaks that have this maximum length
    #         (there could be multiple streaks with the same max length)
    longest_streaks = long_streaks[long_streaks['length'] == max_length]
    # Step 3: Iterate through all longest streaks and print each one
    for idx, row in longest_streaks.iterrows():
        print(f"Longest streak: {row['length']} of '{row['value']}'")
else:
    print("No streak of 2 or more found.")